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Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Carboamination or Carboalkoxylation Reactions

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Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 32))

Abstract

This review describes recent advances over the past decade in the field of heterocycle synthesis via Pd-catalyzed alkene carboamination or carboalkoxylation reactions. These transformations effect the coupling of a carbon electrophile with an unsaturated alcohol or amine and provide heterocyclic products via difunctionalization of the substrate alkene. These reactions provide stereoselective access to a broad array of oxygen and nitrogen heterocycles, including compounds that contain more than one heteroatom. The current scope and limitations of these transformations are discussed, along with relevant mechanistic details.

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References

  1. Wolfe JP, Rossi MA (2004) Stereoselective synthesis of tetrahydrofurans via the palladium-catalyzed reaction of aryl bromides with γ-hydroxy alkenes: evidence for an unusual intramolecular olefin insertion into a Pd(Ar)(OR) intermediate. J Am Chem Soc 126:1620–1621

    CAS  Google Scholar 

  2. Hay MB, Hardin AR, Wolfe JP (2005) Palladium-catalyzed synthesis of tetrahydrofurans from γ-hydroxy terminal alkenes: scope, limitations, and stereoselectivity. J Org Chem 70:3099–3107

    CAS  Google Scholar 

  3. Lasikova A, Dohanosova J, Hlavinova L, Toffano M, Vo-Thanh G, Kozisek J, Gracza T (2012) Domino reaction: Pd(II)-catalyzed cyclization of unsaturated polyols and cross-coupling. Tetrahedron Asymmetry 23:818–827

    CAS  Google Scholar 

  4. Rosen BR, Ney JE, Wolfe JP (2010) Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions. J Org Chem 75:2756–2759

    CAS  Google Scholar 

  5. Hay MB, Wolfe JP (2005) Palladium-catalyzed synthesis of 2,1′-disubstituted tetrahydrofurans from γ-hydroxy internal alkenes. Evidence for alkene insertion into a Pd–O bond and stereochemical scrambling via β-hydride elimination. J Am Chem Soc 127:16468–16476

    CAS  Google Scholar 

  6. Ward AF, Wolfe JP (2010) Highly diastereoselective Pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans. Org Lett 12:1268–1271

    CAS  Google Scholar 

  7. Yeh MCP, Tsao WC, Tu LH (2005) Palladium-catalyzed reaction of aryl bromides with 7-hydroxy-1,3-dienes. Organometallics 24:5909–5915

    CAS  Google Scholar 

  8. Ward AF, Wolfe JP (2009) Synthesis of fused-ring and attached-ring bis-tetrahydrofurans via Pd-catalyzed carboetherification. Org Lett 11:2209–2212

    CAS  Google Scholar 

  9. Nakhla JS, Kampf JW, Wolfe JP (2006) Intramolecular Pd-catalyzed carboetherification and carboamination. Influence of catalyst structure on reaction mechanism and product stereochemistry. J Am Chem Soc 128:2893–2901

    CAS  Google Scholar 

  10. Cacchi S, Fabrizi G, Goggiamani A, Iazzetti A, Madec D, Poli G, Prestat G (2011) Functionalized 2,3-dihydropyrans via palladium-catalyzed oxyarylation of α-allyl-β-ketoesters. Org Biomol Chem 9:8233–8236

    CAS  Google Scholar 

  11. Kim ES, Kim KH, Park S, Kim JN (2010) Synthesis of dihydroindenofuran scaffold via a Pd-catalyzed 5-endo-trig cyclization/enolate O-alkylation cascade. Tetrahedron Lett 51:4648–4652

    CAS  Google Scholar 

  12. Hay MB, Wolfe JP (2007) Stereoselective synthesis of isoxazolidines through Pd-catalyzed carboetherification of N-butenylhydroxylamines. Angew Chem Int Ed 46:6492–6494

    CAS  Google Scholar 

  13. Jiang D, Peng J, Chen Y (2008) Pd-catalyzed carboetherification of β, γ-unsaturated oximes: a novel approach to Δ2-isoxazolines. Org Lett 10:1695–1698

    CAS  Google Scholar 

  14. Hayashi S, Yorimitsu H, Oshima K (2009) Synthesis of epoxides by palladium-catalyzed reactions of tertiary allylic alcohols with aryl or alkenyl halides. J Am Chem Soc 131:2052–2053

    CAS  Google Scholar 

  15. Ward AF, Xu Y, Wolfe JP (2012) Synthesis of chromans via Pd-catalyzed alkene carboetherification reactions. Chem Commun 48:609–611

    CAS  Google Scholar 

  16. Waser J, Nicolai S (2011) Pd(0)-catalyzed oxy- and aminoalkynylation of olefins for the synthesis of tetrahydrofurans and pyrrolidines. Org Lett 13:6324–6327

    Google Scholar 

  17. Nicolai S, Erard S, Fernandez Gonzalez D, Waser J (2010) Pd-catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine. Org Lett 12:384–387

    CAS  Google Scholar 

  18. Zhu R, Buchwald SL (2012) Copper-catalyzed oxytrifluoromethylation of unactivated alkenes. J Am Chem Soc 134:12462–12465

    CAS  Google Scholar 

  19. Zhang G, Cui L, Wang Y, Zhang L (2010) Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes. J Am Chem Soc 132:1474–1475

    CAS  Google Scholar 

  20. Ball LT, Green M, Lloyd-Jones GC, Russell CA (2010) Arylsilanes: application to gold-catalyzed oxyarylation of alkenes. Org Lett 12:4724–4727

    CAS  Google Scholar 

  21. Tkatchouk E, Mankad NP, Benitez D, Goddard WA III, Toste FD (2011) Two metals are better than one in the gold catalyzed oxidative heteroarylation of alkenes. J Am Chem Soc 133:14293–14300

    CAS  Google Scholar 

  22. Zhu C, Falck JR (2011) Alternative pathways for heck intermediates: palladium-catalyzed oxyarylation of homoallylic alcohols. Angew Chem Int Ed 50:6626–6629

    CAS  Google Scholar 

  23. Zhu R, Buchwald SL (2012) Combined oxypalladation/C-H functionalization: palladium(II)-catalyzed intramolecular oxidative oxyarylation of hydroxyalkenes. Angew Chem Int Ed 51: 1926–1929

    CAS  Google Scholar 

  24. Matsuura BS, Condie AG, McBee IA, Buff RC, Karahalis GJ, Stephenson CRJ (2011) Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization. Org Lett 13:6320–6323

    CAS  Google Scholar 

  25. Miller Y, Miao L, Hosseini AS, Chemler SR (2012) Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans. J Am Chem Soc 134:12149–12156

    CAS  Google Scholar 

  26. Fries P, Halter D, Kleinschek A, Hartung J (2011) Functionalized tetrahydrofurans from alkenols and olefins/alkynes via aerobic oxidation-radical addition cascades. J Am Chem Soc 133:3906–3912

    CAS  Google Scholar 

  27. Semmelhack MF, Bodurow C (1984) Intramolecular alkoxypalladation/carbonylation of alkenes. J Am Chem Soc 106:1496–1498

    CAS  Google Scholar 

  28. Semmelhack MF, Zhang N (1989) Stereoselective formation of tetrahydrofuran rings via intramolecular alkoxycarbonylation of hydroxyalkenes. J Org Chem 54:4483–4485

    CAS  Google Scholar 

  29. McCormick M, Monahan R III, Soria J, Goldsmith D, Liotta D (1989) Effects of substitution on intramolecular alkoxypalladation carbonylation reactions. J Org Chem 54:4485–4487

    CAS  Google Scholar 

  30. Semmelhack MF, Kim C, Zhang N, Bodurow C, Sanner M, Dobler W, Meier M (1990) Intramolecular alkoxy-carbonylation of hydroxy alkenes promoted by Pd(II). Pure Appl Chem 62:2035–2040

    CAS  Google Scholar 

  31. Tamaru Y, Kobayashi T, Kawamura S, Ochiai H, Hojo M, Yoshida Z (1985) Palladium catalyzed oxycarbonylation of 4-penten-1,3-diols: efficient stereoselective synthesis of cis-3-hydroxytetrahydrofuran-2-acetic acid lactones. Tetrahedron Lett 26:3207–3210

    CAS  Google Scholar 

  32. Tietze LF, Zinngrebe J, Spiegl DA, Stecker F (2007) Palladium-catalyzed Domino Wacker carbonylation reaction for the enantioselective synthesis of chromans and benzodioxins. Heterocycles 74:473–489

    CAS  Google Scholar 

  33. Semmelhack MF, Epa WR, Cheung AWH, Gu Y, Kim C, Zhang N, Lew W (1994) Palladium-promoted synthesis of ionophore antibiotics. Strategy and assembly of the homochiral tetrahydrofuran and tetrahydropyran portions of tetronomycin. J Am Chem Soc 116:7455–7456

    CAS  Google Scholar 

  34. Paddon-Jones GC, Hungerford NL, Hayes P, Kitching W (1999) Efficient palladium(II)-mediated construction of functionalized plakortone cores. Org Lett 1:1905–1907

    CAS  Google Scholar 

  35. Semmelhack MF, Shanmugam P (2000) Development of an approach to the synthesis of the plakortones. Tetrahedron Lett 41:3567–3571

    CAS  Google Scholar 

  36. Hayes PY, Kitching W (2002) Total synthesis and absolute stereochemistry of plakortone D. J Am Chem Soc 124:9718–9719

    CAS  Google Scholar 

  37. Paddon-Jones GC, McErlean CSP, Hayes P, Moore CJ, Konig WA, Kitching W (2001) Synthesis and stereochemistry of some bicyclic γ-lactones from parasitic wasps (Hymenoptera: Braconidae). Utility of hydrolytic kinetic resolution of epoxides and palladium(II)-catalyzed hydroxycyclization-carbonylation-lactonization of ene-diols. J Org Chem 66:7487–7495

    CAS  Google Scholar 

  38. Babjak M, Kapitan P, Gracza T (2005) Synthesis of (+)-goniothalesdiol and (+)-7-epi-goniothalesdiol. Tetrahedron 61:2471–2479

    CAS  Google Scholar 

  39. Hayes PY, Chow S, Rahm F, Bernhardt PV, DeVoss JJ, Kitching W (2010) Synthesis of the sponge-derived plakortone series of bioactive compounds. J Org Chem 75:6489–6501

    CAS  Google Scholar 

  40. Karlubikova O, Babjak M, Gracza T (2011) Tetrahydropyran synthesis by palladium(II)-catalyzed hydroxycarbonylation of hexenols: synthesis of (±)-diospongin A and (+)-civet cat compound. Tetrahedron 67:4980–4987

    CAS  Google Scholar 

  41. Wu XF, Neumann H, Beller M (2013) Synthesis of heterocycles via palladium-catalyzed carbonylations. Chem Rev 113:1–35

    Google Scholar 

  42. Hoang GT, Reddy VJ, Nguyen HHK, Douglas CJ (2011) Insertion of an alkene into an ester: intramolecular oxyacylation reaction of alkenes through acyl C–O bond activation. Angew Chem Int Ed 50:1882–1884

    CAS  Google Scholar 

  43. Koester DC, Kobayashi M, Werz DB, Nakao Y (2012) Intramolecular oxycyanation of alkenes by cooperative Pd/BPh3 catalysis. J Am Chem Soc 134:6544–6547

    CAS  Google Scholar 

  44. Ney JE, Wolfe JP (2004) Palladium-catalyzed synthesis of N-aryl pyrrolidines from γ-(N-arylamino)alkenes: evidence for chemoselective alkene insertion into Pd–N bonds. Angew Chem Int Ed 43:3605–3608

    Google Scholar 

  45. Ney JE, Hay MB, Yang Q, Wolfe JP (2005) Synthesis of N-aryl-2-allyl pyrrolidines via palladium-catalyzed carboamination reactions of γ-(N-arylamino)alkenes with vinyl bromides. Adv Synth Catal 347:1614–1620

    CAS  Google Scholar 

  46. Neukom JD, Perch NS, Wolfe JP (2010) Intramolecular alkene aminopalladation reactions of (dppf)Pd(Ar)[N(Ar1)(CH2)3CH=CH2] complexes. Insertion of unactivated alkenes into Pd–N bonds. J Am Chem Soc 132:6276–6277

    CAS  Google Scholar 

  47. Neukom JD, Perch NS, Wolfe JP (2011) Intramolecular insertion of alkenes into Pd–N bonds. Effects of substrate and ligand structure on the reactivity of (P–P)Pd(Ar)[N(Ar1)(CH2)3CR=CHR′] complexes. Organometallics 30:1269–1277

    CAS  Google Scholar 

  48. Hanley PS, Markovic D, Hartwig JF (2010) Intermolecular insertion of ethylene and octene into a palladium-amide bond. Spectroscopic evidence for an ethylene amido intermediate. J Am Chem Soc 132:6302–6303

    CAS  Google Scholar 

  49. Hanley PS, Hartwig JF (2011) Intermolecular migratory insertion of unactivated olefins into palladium-nitrogen bonds. Steric and electronic effects on the rate of migratory insertion. J Am Chem Soc 133:15661–15673

    CAS  Google Scholar 

  50. White PB, Stahl SS (2011) Reversible alkene insertion into the Pd–N bond of Pd(II)-sulfonamidates and implications for catalytic amidation reactions. J Am Chem Soc 133:18594–18597

    CAS  Google Scholar 

  51. Ney JE, Wolfe JP (2005) Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction. J Am Chem Soc 127:8644–8651

    CAS  Google Scholar 

  52. Schultz DM, Wolfe JP (2011) Intramolecular alkene carboamination reactions for the synthesis of enantiomerically enriched tropane derivatives. Org Lett 13:2962–2965

    CAS  Google Scholar 

  53. Lira R, Wolfe JP (2004) Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification. J Am Chem Soc 126:13906–13907

    CAS  Google Scholar 

  54. Yang Q, Ney JE, Wolfe JP (2005) Palladium-catalyzed tandem n-arylation/carboamination reactions for the stereoselective synthesis of N-aryl-2-benzylpyrrolidines. Org Lett 7:2575–2578

    CAS  Google Scholar 

  55. Lemen GS, Wolfe JP (2011) Cascade intramolecular N-arylation/intermolecular carboamination reactions for the construction of tricyclic heterocycles. Org Lett 13:3218–3221

    CAS  Google Scholar 

  56. Bertrand MB, Wolfe JP (2005) Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) and γ-(N-boc-amino)alkenes with aryl bromides. Tetrahedron 61:6447–6459

    CAS  Google Scholar 

  57. Tepsen TH, Larsen M, Nielsen MB (2010) On the scope of Pd-catalyzed carboamination reactions-synthesis of 2,4-disubstituted pyrrolidines and 2-substituted piperidines and morpholines. Tetrahedron 66:6133–6137

    Google Scholar 

  58. Bertrand MB, Leathen ML, Wolfe JP (2007) Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions. Org Lett 9:457–460

    CAS  Google Scholar 

  59. Bertrand MB, Neukom JD, Wolfe JP (2008) Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation. J Org Chem 73: 8851–8860

    CAS  Google Scholar 

  60. Bertrand MB, Wolfe JP (2006) A concise stereoselective synthesis of preussin, 3-epi-preussin, and analogues. Org Lett 8:2353–2356

    Google Scholar 

  61. Rossiter LM, Slater ML, Giessert RE, Sakwa SA, Herr RJ (2009) A concise palladium-catalyzed carboamination route to (±)-tylophorine. J Org Chem 74:9554–9557

    CAS  Google Scholar 

  62. Mai DN, Wolfe JP (2010) Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(arylmethyl) and 2-(alkenylmethyl)pyrrolidines. J Am Chem Soc 132:12157–12159

    CAS  Google Scholar 

  63. Mai DN, Rosen BR, Wolfe JP (2011) Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination. Org Lett 13:2932–2935

    CAS  Google Scholar 

  64. Lemen GS, Wolfe JP (2010) Pd-catalyzed carboamination of oxazolidin-2-ones: a stereoselective route to trans-2,5-disubstituted pyrrolidines. Org Lett 12:2322–2325

    CAS  Google Scholar 

  65. Bagnoli L, Cacchi S, Fabrizi G, Goggiamani A, Scarponi C, Tiecco M (2010) Diastereoselective synthesis of hexahydro-3H-pyrrolizidin-3-ones through Pd-catalyzed carboamination. J Org Chem 75:2134–2137

    CAS  Google Scholar 

  66. Jaegli S, Erb W, Retailleau P, Vors JP, Neuville L, Zhu J (2010) Palladium-catalyzed domino process to spirooxindoles: ligand effect on aminopalladation versus carbopalladation. Chemistry 16:5863–5867

    CAS  Google Scholar 

  67. Ward AF, Wolfe JP (2011) Stereoselective synthesis of 1,3-oxazolidines via Pd-catalyzed carboamination reactions of O-vinyl-1,2-amino alcohols. Org Lett 13:4728–4731

    CAS  Google Scholar 

  68. Fritz JA, Nakhla JS, Wolfe JP (2006) A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas. Org Lett 8:2531–2534

    CAS  Google Scholar 

  69. Fritz JA, Wolfe JP (2008) Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations. Tetrahedron 64:6838–6852

    CAS  Google Scholar 

  70. Babij NR, Wolfe JP (2012) Asymmetric total synthesis of (+)-merobatzelladine B. Angew Chem Int Ed 51:4128–4130

    CAS  Google Scholar 

  71. Hopkins BA, Wolfe JP (2012) Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric Pd-catalyzed carboamination reactions. Angew Chem Int Ed 51:9886–9890

    CAS  Google Scholar 

  72. Giampietro NC, Wolfe JP (2008) Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via Pd-catalyzed carboamination reactions. Use of allylic strain to control product stereochemistry through N-substituent manipulation. J Am Chem Soc 130:12907–12911

    CAS  Google Scholar 

  73. Lemen GS, Giampietro NC, Hay MB, Wolfe JP (2009) Influence of hydroxylamine conformation on stereocontrol in Pd-catalyzed isoxazolidine-forming reactions. J Org Chem 74:2533–2540

    CAS  Google Scholar 

  74. Peng J, Lin W, Yuan S, Chen Y (2007) J Org Chem 72:3145–3148

    CAS  Google Scholar 

  75. Hayashi S, Yorimitsu H, Oshima K (2009) Synthesis of aziridines by palladium-catalyzed reactions of allylamines with aryl and alkenyl halides. Evidence of a syn-carboamination pathway. Angew Chem Int Ed 48:7224–7226

    CAS  Google Scholar 

  76. Nakhla JS, Wolfe JP (2007) A concise asymmetric synthesis of cis-2,6-disubstituted N-aryl piperazines via Pd-catalyzed carboamination reactions. Org Lett 9:3279–3282

    CAS  Google Scholar 

  77. Nakhla JS, Schultz DM, Wolfe JP (2009) Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines. Tetrahedron 65:6549–6570

    CAS  Google Scholar 

  78. Leathen ML, Rosen BR, Wolfe JP (2009) New strategy for the synthesis of substituted morpholines. J Org Chem 74:5107–5110

    CAS  Google Scholar 

  79. Neukom JD, Aquino AS, Wolfe JP (2011) Synthesis of saturated 1,4-benzodiazepines via Pd-catalyzed carboamination reactions. Org Lett 13:2196–2199

    CAS  Google Scholar 

  80. Nicolai S, Piemontesi C, Waser J (2011) A palladium-catalyzed aminoalkynylation strategy towards bicyclic heterocycles: synthesis of (±)-trachelanthamidine. Angew Chem Int Ed 50: 4680–4683

    CAS  Google Scholar 

  81. Brenzovich WE Jr, Benitez D, Lackner AD, Shunatona HP, Tkatchouk E, Goddard WA III, Toste FD (2010) Gold-catalyzed intramolecular aminoarylation of alkenes: C–C bond formation through bimolecular reductive elimination. Angew Chem Int Ed 49:5519–5522

    CAS  Google Scholar 

  82. Sherman ES, Chemler SR, Tan TB, Gerlits O (2004) Copper(II) acetate-promoted oxidative cyclization of arylsulfonyl-o-allylanilines. Org Lett 6:1573–1575

    CAS  Google Scholar 

  83. Sherman ES, Fuller PH, Kasi D, Chemler SR (2007) Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism. J Org Chem 72:3896–3905

    CAS  Google Scholar 

  84. Sherman ES, Chemler SR (2009) Copper(II)-catalyzed aminooxygenation and carboamination of N-aryl-2-allylanilines. Adv Synth Catal 351:467–471

    CAS  Google Scholar 

  85. Fuller PH, Chemler SR (2007) Copper(II) carboxylate-promoted intramolecular carboamination of alkenes for the synthesis of polycyclic lactams. Org Lett 9:5477–5480

    CAS  Google Scholar 

  86. Zeng W, Chemler SR (2007) Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes. J Am Chem Soc 129:12948–12949

    CAS  Google Scholar 

  87. Zheng W, Chemler SR (2008) Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination. J Org Chem 73:6045–6047

    Google Scholar 

  88. Miao L, Haque I, Manzoni MR, Tham WS, Chemler SR (2010) Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles. Org Lett 12:4739–4741

    CAS  Google Scholar 

  89. Liwosz TW, Chemler SR (2012) Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular Heck-type coupling cascade. J Am Chem Soc 134:2020–2023

    CAS  Google Scholar 

  90. Yip KT, Yang D (2011) Pd(II)-catalyzed intramolecular amidoarylation of alkenes with molecular oxygen as the sole oxidant. Org Lett 13:2134–2137

    CAS  Google Scholar 

  91. Jaegli S, Dufour J, Wei HI, Piou T, Duan XH, Vors JP, Neuville L, Zhu J (2010) Palladium-catalyzed carbo-heterofunctionalization of alkenes for the synthesis of oxindoles and spirooxindoles. Org Lett 12:4498–4501

    CAS  Google Scholar 

  92. Rosewall CF, Sibbald PA, Liskin DV, Michael FE (2009) Palladium-catalyzed carboamination of alkenes promoted by N-fluorobenzenesulfonimide via C–H activation of arenes. J Am Chem Soc 131:9488–9489

    CAS  Google Scholar 

  93. Sibbald PA, Rosewall CF, Swartz RD, Michael FE (2009) Mechanism of N-fluorobenzenesulfonimide promoted diamination and carboamination reactions: divergent reactivity of a Pd(IV) species. J Am Chem Soc 131:15945–15951

    CAS  Google Scholar 

  94. Jana R, Pathak TP, Jensen KH, Sigman MS (2012) Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives. Org Lett 14:4074–4077

    CAS  Google Scholar 

  95. Zhang G, Luo Y, Wang Y, Zhang L (2011) Combining gold(I)/Gold(III) catalysis and C–H functionalization: a formal intramolecular [3+2] annulation towards tricyclic indolines and mechanistic studies. Angew Chem Int Ed 50:4450–4454

    CAS  Google Scholar 

  96. Schultz DM, Wolfe JP (2010) Synthesis of polycyclic nitrogen heterocycles via alkene aminopalladation/carbopalladation cascade reactions. Org Lett 12:1028–1031

    CAS  Google Scholar 

  97. Yip KT, Yang D (2011) Palladium(II)-catalyzed oxidative cascade cyclization reactions of anilides and anilines: scope and mechanistic investigations. Chem Asian J 6:2166–2175

    CAS  Google Scholar 

  98. He W, Yip KT, Zhu NY, Yang D (2009) Pd(II)/tBu-quinolineoxazoline: an air-stable and modular chiral catalyst system for enantioselective oxidative cascade cyclization. Org Lett 11:5626–5628

    CAS  Google Scholar 

  99. Scarborough CC, Stahl SS (2006) Synthesis of pyrrolidines via palladium(II)-catalyzed aerobic oxidative carboamination of butyl vinyl ether and styrenes with allyl tosylamides. Org Lett 8:3251–3254

    CAS  Google Scholar 

  100. Tamaru Y, Kobayashi T, Kawamura S, Ochiai H, Yoshida Z (1985) Stereoselective intramolecular aminocarbonylation of 3-hydroxypent-4-enylamides catalyzed by palladium. Tetrahedron Lett 26:4479–4482

    CAS  Google Scholar 

  101. Tamaru Y, Hojo M, Higashimura H, Yoshida Z (1988) Urea as the most reactive and versatile nitrogen nucleophile for the palladium(2+)-catalyzed cyclization of unsaturated amines. J Am Chem Soc 110:3994–4002

    CAS  Google Scholar 

  102. Tamaru Y, Hojo M, Yoshida Z (1988) Palladium(2+)-catalyzed intramolecular aminocarbonylation of 3-hydroxy-4-pentenylamines and 4-hydroxy-5-hexenylamines. J Org Chem 53: 5731–5741

    CAS  Google Scholar 

  103. Tamaru Y, Tanigawa H, Ito S, Kimura M, Tanaka S, Fugami K, Sekiyama T, Yoshida Z (1992) Palladium(II)-catalyzed oxidative aminocarbonylation of unsaturated carbamates. Tetrahedron Lett 33:631–634

    CAS  Google Scholar 

  104. Harayama H, Okuno H, Takahashi Y, Kimura M, Fugami K, Tanaka S, Tamaru Y (1996) Chemoselective intramolecular aminocarbonylation of unsaturated amides under Wacker-type conditions. Tetrahedron Lett 37:7287–7290

    CAS  Google Scholar 

  105. Harayama H, Abe A, Sakado T, Kimura M, Fugami K, Tanaka S, Tamaru Y (1997) Palladium(II)-catalyzed intramolecular aminocarbonylation of endo-carbamates under Wacker-type conditions. J Org Chem 62:2113–2122

    CAS  Google Scholar 

  106. Borsini E, Broggini G, Fasana A, Galli S, Khansaa M, Piarulli U, Rigamonti M (2011) Intramolecular palladium-catalyzed aminocarboxylation of olefins as a direct rouge to bicyclic oxazolidinones. Adv Synth Catal 353:985–994

    CAS  Google Scholar 

  107. Shinohara T, Arai MA, Wakita K, Arai T, Sasai H (2003) The first enantioselective intramolecular aminocarbonylation of alkenes promoted by Pd(II)-spiro bis(isoxazoline) catalyst. Tetrahedron Lett 44:711–714

    CAS  Google Scholar 

  108. Tsujihara T, Shinohara T, Takenaka K, Takizawa S, Onitsuka K, Hatanaka M, Sasai H (2009) Enantioselective intramolecular oxidative aminocarbonylation of alkenylureas catalyzed by palladium-spiro bis(isoxazoline) complexes. J Org Chem 74:9274–9279

    CAS  Google Scholar 

  109. Koos P, Spanik I, Gracza T (2009) Asymmetric Pd(II)-catalyzed amidocarbonylation of unsaturated amino alcohols. Tetrahedron Asymmetry 20:2720–2723

    CAS  Google Scholar 

  110. Oh CY, Kim KS, Ham WH (1998) A formal synthesis of (±)-anatoxin A by an intramolecular Pd-catalyzed aminocarbonylation reaction. Tetrahedron Lett 39:2133–2136

    CAS  Google Scholar 

  111. Kubizna P, Spanik I, Kozisek J, Szolcsanyi P (2010) Synthesis of 2,6-disubstituted piperidine alkaloids from ladybird beetles Calvia 10-guttata and Calvia 14-guttata. Tetrahedron 66:2351–2355

    CAS  Google Scholar 

  112. Csatayova K, Spanik I, Durisova V, Szolcsanyi P (2010) Synthesis of (−)-pinidinone. Tetrahedron Lett 51:6611–6614

    CAS  Google Scholar 

  113. Szolcsanyi P, Gracza T, Koman M, Pronayova N, Liptaj T (2000) Pd(II)-catalyzed aminocarbonylation as a key step in the total synthesis of C-6 homologues of 1-deoxynojirimycin and 1-deoxy-l-idonojirimycin. Tetrahedron Asymmetry 11:2579–2597

    CAS  Google Scholar 

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  1. Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI, 48109-1055, USA

    John P. Wolfe

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    John P. Wolfe

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Wolfe, J.P. (2013). Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Carboamination or Carboalkoxylation Reactions. In: Wolfe, J. (eds) Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds. Topics in Heterocyclic Chemistry, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2012_98

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