Amino acid mediated borane reduction of ketones II

A. V. Teodorović, M. D. Joksović, I. Gutman, Ž Tomović

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)

Abstract

Acetophenone, 2,2-dimethylcyclopentanone, 3,3-dimethyl-2-butanone, 3-methyl-2-butanone, and 2-pentanone were reduced with borane mediated by (S)-alanine, (S)-methionine, (S)-leucine, (S)-valine, and (S)-isoleucine in very good yields giving predominantly alcohols of (R)-configuration (ee = 23-89%). A molecular topology based model was developed for describing the influence of the substituents, both in the oxazaborolidine type reagent and in the ketone, on the observed chiral induction.

Original languageEnglish
Pages (from-to)23-29
Number of pages7
JournalMonatshefte fur Chemie
Volume133
Issue number1
DOIs
Publication statusPublished - 1 Jan 2002
Externally publishedYes

Keywords

  • (S)-Amino acids
  • Alcohols
  • Chiral induction
  • Ketones
  • Molecular topology based model

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