Molecular-level chiral discrimination and induction

Kazuhiko Saigo, Yukihiko Hashimoto, Kazushi Kinbara, Atsushi Sudo

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

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 2,-columns and planar boundary surfaces in its crystal structure. On the basis of this knowledge, we developed several artificial chiral auxiliaries such as erythro2-amino-l,2-diphenylethanol, cis-2-amino-l-acenaphthenol, and cis-2- amino-3,3dimethyl-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.

Original languageEnglish
Pages (from-to)555-573
Number of pages19
JournalProceedings of the Indian Academy of Sciences: Chemical Sciences
Volume108
Issue number6
DOIs
Publication statusPublished - 1996

Keywords

  • Artificial chiral auxiliaries
  • Chiral discrimination
  • Chiral induction
  • Diastereomeric salts
  • Racemic amines

ASJC Scopus subject areas

  • Chemistry(all)

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