Prolinate Salt as a Catalyst in the syn -Selective, Asymmetric Mannich Reaction of Alkynyl Imine

Yujiro Hayashi, Tatsuya Yamazaki, Genki Kawauchi, Itaru Sato

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Prolinate salt is an efficient catalyst in the Mannich reaction of alkynyl imine and aldehyde, to afford synthetically useful chiral propargyl amine derivatives with excellent syn-selectivity and nearly perfect control of the absolute configuration. The counterion of the prolinate salt does not affect the enantioselectivity. This is a rare example, in which proline alkali metals, alkaline-earth metals, or ammonium salt show higher reactivity and better stereoselectivity than the parent proline.

Original languageEnglish
Pages (from-to)2391-2394
Number of pages4
JournalOrganic letters
Volume20
Issue number8
DOIs
Publication statusPublished - 2018 Apr 20

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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