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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/108/06/0555-0573

    • Keywords

       

      Chiral discrimination; chiral induction; artificial chiral auxiliaries; racemic amines; diastereomeric salts

    • Abstract

       

      The review describes the mechanism of chiral discrimination of racemic amines upon crystallization and the induction of chirality in organic reactions by using them as chiral auxiliaries. In order to form conglomerates, which can be resolved into the two enantiomers upon alternative seeding, both formation and packing of 21-columns are essentially very important. On the other hand, in order to achieve high efficiency in resolution through diastereomeric salt formation, which is the most practical method, one of a pair of diastereomeric salts derived from a racemic amine and an enantiomerically pure resolving agent should at least have two 21-columns and planar boundary surfaces in its crystal structure. On the basis of this knowledge, we developed several artificial chiral auxiliaries such as erythro-2-amino-1,2-diphenylethanol,cis-2-amino-1-acenaphthenol, andcis-2-amino-3,3-dimethyl-1-indanol. These were found to be very efficient chiral auxiliaries in asymmetric inductions: alkylation of chiral imines, catalytic borane-reduction, and alkylation of chiral N-acylated oxazolidinone.

    • Author Affiliations

       

      Kazuhiko Saigo1 Yukihiko Hashimoto1 Kazushi Kinbara1 Atsushi Sudo1

      1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo - 113, Japan
    • Dates

       
  • Journal of Chemical Sciences | News

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