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Targeting the Remote Control of Axial Chirality in N-(2-tert-butylphenyl)Succinimides via a Desymmetrization Strategy

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New Organocatalytic Strategies for the Selective Synthesis of Centrally and Axially Chiral Molecules

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Abstract

There are molecules possessing stereogenic elements that are not chiral. These compounds are termed “meso” and do not manifest chirality because they possess a symmetry element of the second order (i.e. a symmetry plane)2 that makes their mirror images superimposable (Fig. 3.1).

Meso form of tartaric acid

Published as: References [1,2,3].

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Notes

  1. 1.

    For further reading on desymmetrization see: [5, 6].

  2. 2.

    We have already talked in Sect. 2.1 about the issues arising from vinylogous reactivity where usually the stereogenic carbons are three or four bonds away from the activated site of the molecule therefore the challenge of forging a stereogenic element seven bonds away is even more formidable.

  3. 3.

    The absolute configuration was determined via single crystal XRD of the corresponding brominated product 149a and assigned by analogy to 137a.

  4. 4.

    See the experimental section for details.

  5. 5.

    A value of 31.9 kcal/mol corresponds roughly to a half life of epimerization of 1000 years.

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Authors and Affiliations

  1. Department of Industrial Chemistry “Toso Montanari”, University of Bologna, Bologna, Italy

    Nicola Di Iorio

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  1. Nicola Di Iorio
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Correspondence to Nicola Di Iorio .

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Di Iorio, N. (2018). Targeting the Remote Control of Axial Chirality in N-(2-tert-butylphenyl)Succinimides via a Desymmetrization Strategy. In: New Organocatalytic Strategies for the Selective Synthesis of Centrally and Axially Chiral Molecules. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-74914-3_3

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