Direct enantioselective amination of α-ketoesters catalyzed by an axially chiral guanidine base

Masahiro Terada, Kei Amagai, Kenichi Ando, Eunsang Kwon, Hitoshi Ube

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

β-functional! Direct enantioselective amination of α-ketoesters with azodicarboxylates was demonstrated using an axially chiral guanidine base catalyst, which enabled efficient access to enantioenriched multifunctionalized ketoesters with an aliphatic substituent at the β-position. Subsequent nucleophilic addition to the β-hydrazinyl-α-ketoester at the reactive ketone yields the corresponding β-hydrazinyl-α-hydroxy esters in high syn diastereo- and enantioselectivities (see scheme).

Original languageEnglish
Pages (from-to)9037-9041
Number of pages5
JournalChemistry - A European Journal
Volume17
Issue number33
DOIs
Publication statusPublished - 2011 Aug 8

Keywords

  • amino alcohols
  • asymmetric catalysis
  • enantioselectivity
  • guanidine
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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