Enantioselective electrophilic amination of α-cyanothioacetates with azodicarboxylates catalyzed by an axially chiral guanidine base

Masahiro Terada, Daisuke Tsushima, Megumi Nakano

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

An enantioselective electrophilic amination of α-substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Brønsted base catalyst. The corresponding product, having a quaternary stereogenie center at the α-carbon atom, is formed in excellent enantioselectivity.

Original languageEnglish
Pages (from-to)2817-2821
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume351
Issue number17
DOIs
Publication statusPublished - 2009 Nov 1

Keywords

  • Amination
  • Amino acids
  • Asymmetric catalysis
  • Organocatalysis
  • Quaternary stereocenters

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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