Skip to main content
SpringerLink
Log in

Synthesis of Saturated Heterocycles via Metal-Catalyzed Allylic Alkylation Reactions

  • Chapter
  • First Online:
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

Over the past 10 years, significant progress has been made in the field of metal-catalyzed allylic alkylation reactions. Intramolecular variants forming saturated heterocycles comprise a well-known class of reactions that are often utilized in the syntheses of biologically active natural products. Selected recent advances in this area between the years 2002 and 2012 and their applications toward total syntheses are reviewed herein.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Abbreviations

(R)-BINAPHANE:

(R,R)-1,2-Bis[(R)-4,5-dihydro-3H-binaptho-(1,2c:2′,1′e)phosphino]benzene

Ac:

Acetyl

Bn:

Benzyl

Boc:

t-Butoxycarbonyl

Bz:

Benzoyl

Cbz:

Benzyloxycarbonyl

cod:

1,5-Cyclooctadiene

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DACH-Ph:

1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphinobenzoyl)

dba:

Dibenzylideneacetone

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DMPS:

Dimethylphenylsilyl

DPPBA:

Diphenylphosphinobenzoic acid

dppe:

1,2-Bis(diphenylphosphino)ethane

Fmoc:

9-Fluorenylmethoxycarbonyl

MeO-BIPHEP:

2,2′-Bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl

Ns:

2-Nitrobenzenesulfonyl

Ph:

Phenyl

PMB:

p-Methoxybenzyl

PMP:

p-Methoxyphenyl

TBD:

1,5,7-Triazabicyclo-[4.4.0]undec-5-ene

Tf:

Trifluoromethanesulfonyl

TMS:

Trimethylsilyl

Troc:

2,2,2-Trichloroethoxycarbonyl

Ts:

p-Toluenesulfonyl

References

  1. Tsuji J, Takahashi H, Marikawa M (1965) Tetrahedron Lett 6:4387–4388

    Article  Google Scholar 

  2. Trost BM, Fullerton TJ (1973) J Am Chem Soc 95:292–294

    Article  CAS  Google Scholar 

  3. Lu Z, Ma S (2008) Angew Chem Int Ed 47:258–297

    Article  CAS  Google Scholar 

  4. Trost BM, Zhang T, Sieber JD (2010) Chem Sci 1:427–440

    Article  CAS  Google Scholar 

  5. Trost BM (2012) Org Process Res Dev 16:185–194

    Article  CAS  Google Scholar 

  6. Trost BM, Genet JP (1976) J Am Chem Soc 98:8516–8517

    Article  CAS  Google Scholar 

  7. Trost BM, Godleski SA (1978) J Am Chem Soc 100:3930–3931

    Article  CAS  Google Scholar 

  8. Trost BM, Oslob JD (1999) J Am Chem Soc 121:3057–3064

    Article  CAS  Google Scholar 

  9. Williams DR, Meyer KG (1999) Org Lett 1:1303–1305

    Article  CAS  Google Scholar 

  10. Seki M, Mori Y, Hatsuda M, Yamada S (2002) J Org Chem 67:5527–5536

    Article  CAS  Google Scholar 

  11. Graenin T, Schmalz HG (2003) Angew Chem Int Ed 42:2580–2584

    Article  Google Scholar 

  12. Trost BM, Naoyuki A (1999) Synthesis 1491–1494

    Google Scholar 

  13. Trost BM, Shen HC, Dong L, Surivet JP (2003) J Am Chem Soc 125:9276–9277

    Article  CAS  Google Scholar 

  14. Trost BM, Shen HC, Dong L, Surivet JP, Sylvain C (2004) J Am Chem Soc 126:11966–11983

    Article  CAS  Google Scholar 

  15. Trost BM, Shen HC, Surivet JP (2004) J Am Chem Soc 126:12565–12579

    Article  CAS  Google Scholar 

  16. Trost BM, Dong G (2006) J Am Chem Soc 128:6054–6055

    Article  CAS  Google Scholar 

  17. Trost BM, Dong G (2009) Chem Eur J 15:6910–6919

    Article  CAS  Google Scholar 

  18. Bisceglia JA, Orelli LR (2012) Curr Org Chem 16:2206–2230

    Article  CAS  Google Scholar 

  19. Cruz AD, He A, Thanavaro A, Yan B, Spilling CD, Rath NP (2005) J Organomet Chem 690:2577–2592

    Article  Google Scholar 

  20. He A, Sutivisedsak N, Spilling CD (2009) Org Lett 11:3124–3127

    Article  CAS  Google Scholar 

  21. Roy S, Spilling CD (2010) Org Lett 12:5326–5329

    Article  CAS  Google Scholar 

  22. Roy S, Spilling CD (2012) Org Lett 14:2230–2233

    Article  CAS  Google Scholar 

  23. Tsukanov SV, Comins DL (2011) Angew Chem Int Ed 50:8626–8628

    Article  CAS  Google Scholar 

  24. Tokuyama T, Nishimori N, Shimada A, Edwards MW, Daly JW (1987) Tetrahedron 43:643–657

    Article  CAS  Google Scholar 

  25. Tokuyama T, Garraffo HM, Spande TF, Daly JW (1989) An Asoc Quim Argent 86:291–298

    Google Scholar 

  26. Tsuneki H, You Y, Toyooka N, Kagawa S, Kobayashi S, Sasaoka T, Nemoto H, Kimura I, Dani JA (2004) Mol Pharmacol 66:1061–1069

    Article  CAS  Google Scholar 

  27. Takeuchi R, Kasio M (1997) Angew Chem Int Ed 36:263–265

    Article  CAS  Google Scholar 

  28. Takeuchi R, Kasio M (1998) J Am Chem Soc 120:8647–8655

    Article  CAS  Google Scholar 

  29. Janssen JP, Helmchen G (1997) Tetrahedron Lett 38:8025–8026

    Article  CAS  Google Scholar 

  30. Bartels B, Helmchen G (1999) Chem Commun 741–742

    Google Scholar 

  31. Hartwig JF, Stanley LM (2010) Acc Chem Res 42:1461–1465

    Article  Google Scholar 

  32. Hartwig JF, Pouy MJ (2011) Top Organomet Chem 34:169–208

    Article  CAS  Google Scholar 

  33. Miyabe H, Yoshida K, Kobayashi Y, Matsumura A, Takemoto Y (2003) Synlett 1031–1033

    Google Scholar 

  34. Welter C, Koch O, Lipowsky F, Helmchen G (2004) Chem Commun 896–897

    Google Scholar 

  35. Welter C, Dahnz A, Brunner B, Streiff S, Dubon P, Helmchen G (2005) Org Lett 7:1239–1242

    Article  CAS  Google Scholar 

  36. Teichert JF, Feringa BL (2010) Angew Chem Int Ed 49:2486–2528

    Article  CAS  Google Scholar 

  37. Gnamm C, Krauter CM, Brodner K, Helmchen G (2009) Chem Eur J 15:2050–2054

    Article  CAS  Google Scholar 

  38. Gnamm C, Brodner K, Krauter CM, Helmchen G (2009) Chem Eur J 15:10514–10532

    Article  CAS  Google Scholar 

  39. Teichert JF, Fananas-Mastral M, Feringa BL (2011) Angew Chem Int Ed 50:688–691

    Article  CAS  Google Scholar 

  40. Berkowitz DB, Maiti G (2004) Org Lett 6:2661–2664

    Article  CAS  Google Scholar 

  41. Berkowitz DB, Shen W, Maiti G (2004) Tetrahedron: Asymmetry 15:2845–2851

    Article  CAS  Google Scholar 

  42. Minami I, Shimizu I, Tsuji J (1985) J Organomet Chem 296:269–280

    Article  CAS  Google Scholar 

  43. Zhang SW, Mitsudo T, Kondo T, Watanabe Y (1993) J Organomet Chem 450:197–207

    Article  CAS  Google Scholar 

  44. Trost BM, Fraisse PL, Ball ZT (2002) Angew Chem Int Ed 41:1059–1061

    Article  CAS  Google Scholar 

  45. Tanaka S, Saburi H, Ishibashi Y, Kitamura M (2004) Org Lett 6:1873–1875

    Article  CAS  Google Scholar 

  46. Saburi H, Tanaka S, Kitamura M (2005) Angew Chem Int Ed 44:1730–1732

    Article  CAS  Google Scholar 

  47. Tanaka S, Seki T, Kitamura M (2009) Angew Chem Int Ed 48:8948–8951

    Article  CAS  Google Scholar 

  48. Seki T, Tanaka S, Kitamura M (2012) Org Lett 14:608–611

    Article  CAS  Google Scholar 

  49. Hirai Y, Terada T, Amemiya Y, Momose T (1992) Tetrahedron Lett 33:7893–7894

    Article  CAS  Google Scholar 

  50. Hirai Y, Nagatsu M (1994) Chem Lett 21–22

    Google Scholar 

  51. Hirai Y, Watanabe J, Nozaki T, Yokoyama H, Yamauchi S (1997) J Org Chem 62:776–777

    Article  CAS  Google Scholar 

  52. Yokoyama H, Otaya K, Yamaguchi S, Hirai Y (1998) Tetrahedron Lett 39:5971–5974

    Article  CAS  Google Scholar 

  53. Yokoyama H, Otaya K, Kobayashi H, Miyazawa M, Yamaguchi S, Hirai Y (2000) Org Lett 2:2427–2429

    Article  CAS  Google Scholar 

  54. Uenishi J, Ohmi M, Ueda A (2005) Tetrahedron: Asymmetry 16:1299–1303

    Article  CAS  Google Scholar 

  55. Uenishi J, Ohmi M (2005) Angew Chem Int Ed 44:2756–2760

    Article  CAS  Google Scholar 

  56. Kawai N, Lagrange JM, Uenishi J (2007) Eur J Org Chem 2808–2814

    Google Scholar 

  57. Palimkar SS, Uenishi J, Ii H (2012) J Org Chem 77:388–399

    Article  CAS  Google Scholar 

  58. Hande SM, Kawai N, Uenishi J (2009) J Org Chem 74:244–253

    Article  CAS  Google Scholar 

  59. Uenishi J, Fujikura Y, Kawai N (2011) Org Lett 13:2350–2353

    Article  CAS  Google Scholar 

  60. Palmes JA (2012) Ph.D. Thesis, University of Florida

    Google Scholar 

  61. Borrero NV, Aponick A (2012) J Org Chem 77:8410–8416

    Article  CAS  Google Scholar 

  62. Awasaguchi K, Miyazawa M, Uoya I, Inoue K, Nakamura K, Yokoyama H, Kakuda H, Hirai Y (2010) Synlett 2010:2392–2396

    Article  Google Scholar 

  63. Li Z, Brouwer C, He C (2008) Chem Rev 108:3239–3265

    Article  CAS  Google Scholar 

  64. Corma A, Peyva-Perez A, Sabater MJ (2011) Chem Rev 111:1657–1712

    Article  CAS  Google Scholar 

  65. Rudolph M, Hashmi ASK (2011) Chem Commun 47:6536–6544

    Article  CAS  Google Scholar 

  66. Biannic B, Aponick A (2011) Eur J Org Chem 6605–6617

    Google Scholar 

  67. Aponick A, Li CY, Biannic B (2008) Org Lett 10:669–671

    Article  CAS  Google Scholar 

  68. Aponick A, Biannic B (2008) Synthesis 3356–3359

    Google Scholar 

  69. Aponick A, Li CY, Palmes JA (2009) Org Lett 11:121–124

    Article  CAS  Google Scholar 

  70. Aponick A, Li CY, Malinge J, Marques EF (2009) Org Lett 11:4624–4627

    Article  CAS  Google Scholar 

  71. Aponick A, Biannic B, Jong MR (2010) Chem Commun 46:6849–6851

    Article  CAS  Google Scholar 

  72. Bandini M, Monari M, Romaniello A, Tragni M (2010) Chem Eur J 16:14272–14277

    Article  CAS  Google Scholar 

  73. Unsworth WP, Stevens K, Lamont SG, Robertson J (2011) Chem Commun 47:7659–7661

    Article  CAS  Google Scholar 

  74. Aponick A, Biannic B (2011) Org Lett 13:1330–1333

    Article  CAS  Google Scholar 

  75. Biannic B, Ghebreghiorgis T, Aponick A (2011) Beilstein J Org Chem 7:802–807

    Article  CAS  Google Scholar 

  76. Mukherjee P, Widenhoefer RA (2011) Org Lett 13:1334–1337

    Article  CAS  Google Scholar 

  77. Mukherjee P, Widenhoefer RA (2012) Angew Chem Int Ed 51:1405–1407

    Article  CAS  Google Scholar 

  78. Ghebreghiorgis T, Biannic B, Kirk BH, Ess DH, Aponick A (2012) J Am Chem Soc 134:16307–16318

    Article  CAS  Google Scholar 

  79. Namba K, Nakagawa Y, Yamamoto H, Imagawa H, Nishizawa M (2008) Synlett 1719–1723

    Google Scholar 

  80. Yamamoto H, Ho E, Namba K, Imagawa H, Nishizawa M (2010) Chem Eur J 16:11271–11274

    Article  CAS  Google Scholar 

  81. Kawai N, Abe R, Uenishi J (2009) Tetrahedron Lett 50:6580–6583

    Article  CAS  Google Scholar 

  82. Kawai N, Abe R, Matsuda M, Uenishi J (2011) J Org Chem 76:2102–2114

    Article  CAS  Google Scholar 

  83. Kawai N, Matsuda M, Uenishi J (2011) Tetrahedron 67:8648–8653

    Article  CAS  Google Scholar 

  84. Xu Z, Li Q, Zhang L, Jia Y (2009) J Org Chem 74:6859–6862

    Article  CAS  Google Scholar 

  85. Xu Z, Hu W, Liu Q, Zhang L, Jia Y (2010) J Org Chem 75:7626–7635

    Article  CAS  Google Scholar 

  86. Jiang D, Xu Z, Jia Y (2012) Tetrahedron 68:4225–4232

    Article  CAS  Google Scholar 

  87. Kothandaraman P, Foo SJ, Chan PWH (2009) J Org Chem 74:5947–5952

    Article  CAS  Google Scholar 

  88. Guerinot A, Serra-Muns A, Gnamm C, Bensoussan C, Reymond S, Cossy J (2010) Org Lett 12:1808–1811

    Article  CAS  Google Scholar 

  89. Guerinot A, Serra-Muns A, Gnamm C, Bensoussan C, Reymond S, Cossy J (2011) Tetrahedron 67:5024–5033

    Article  CAS  Google Scholar 

  90. Wang Z, Li S, Yu B, Wu H, Wang Y, Sun X (2012) J Org Chem 77:8615–8620

    Article  CAS  Google Scholar 

  91. Hanessian S, Focken T, Oza R (2010) Org Lett 12:3172–3175

    Article  CAS  Google Scholar 

  92. Hanessian S, Focken T, Oza R (2011) Tetrahedron 67:9870–9884

    Article  CAS  Google Scholar 

  93. Trost BM, Machacek MR, Faulk BD (2006) J Am Chem Soc 128:6745–6754

    Article  CAS  Google Scholar 

  94. He H, Lie WB, Dai LX, You SL (2010) Angew Chem Int Ed 49:1496–1499

    Article  CAS  Google Scholar 

  95. Davies HML, Du Bois J, Yu JQ (2011) Chem Soc Rev 40:1855–1856

    Article  CAS  Google Scholar 

  96. Mei TS, Kou L, Ma S, Engle KM, Yu JQ (2012) Synthesis 44:1778–1791

    Article  CAS  Google Scholar 

  97. Fraunhoffer KJ, White MC (2007) J Am Chem Soc 129:7274–7276

    Article  CAS  Google Scholar 

  98. Rice GT, White MC (2009) J Am Chem Soc 131:11707–11711

    Article  CAS  Google Scholar 

  99. Stang EM, White MC (2009) Nat Chem 1:547–551

    Article  CAS  Google Scholar 

  100. Qi X, Rice GT, Lall MS, Plummer MS, White MC (2010) Tetrahedron 66:4816–4826

    Article  CAS  Google Scholar 

  101. Gormisky PE, White MC (2011) J Am Chem Soc 133:12584–12589

    Article  CAS  Google Scholar 

  102. Stang EM, White MC (2011) Angew Chem Int Ed 50:2094–2097

    Article  CAS  Google Scholar 

  103. Paradine SM, White MC (2012) J Am Chem Soc 134:2036–2039

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Florida, 117200, Gainesville, 32611, FL, USA

    John M. Ketcham & Aaron Aponick

Authors
  1. John M. Ketcham
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Aaron Aponick
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aaron Aponick .

Editor information

Editors and Affiliations

  1. Department of Chemistry, University of Michigan, Ann Arbor, Michigan, USA

    John P. Wolfe

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Ketcham, J.M., Aponick, A. (2013). Synthesis of Saturated Heterocycles via Metal-Catalyzed Allylic Alkylation 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_2013_103

Download citation

Publish with us

Policies and ethics

Search

Navigation