Enantioselective borodeuteride reduction of aldimines catalyzed by cobalt complexes: Preparation of optically active deuterated primary amines

Daichi Miyazaki, Kohei Nomura, Tatsuya Yamashita, Izumi Iwakura, Taketo Ikeno, Tohru Yamada

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

[Equation presented] The enantioselective borodeuteride reduction catalyzed by optically active β-ketoiminato cobalt complexes was applied to N-(di(o-tolyl)phosphinyl)-aldimines to afford the corresponding optically active deuterated primary amines in high yields with high enantiomeric excesses after simple deprotection. The present deuteride reduction of aldimines is in the opposite sense of the enantioselective for the previously reported borohydride reduction of ketones or diphenylphosphinyl aldimines. The stereochemical course in these enantioselective reductions is discussed.

Original languageEnglish
Pages (from-to)3555-3558
Number of pages4
JournalOrganic Letters
Volume5
Issue number20
DOIs
Publication statusPublished - 2003 Oct 2

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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