Metal-free, enantioselective strecker reactions catalyzed by chiral BINOL and TADDOL catalysts

Magnus Rueping*, Erli Sugiono, Stefan A. Moreth

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

120 Scopus citations

Abstract

An efficient, metal-free Brønsted acid-catalyzed, enantioselective hydrocyanation of ketoimines has been developed. This BINOL phosphate-catalyzed Strecker reaction provides the corresponding amino nitriles, precursors of quaternary amino acids, in good isolated yields and enantioselectivities. Additionally, we demonstrate that chiral diols, such as TADDOL, are effective enantioselective catalysts for the hydrogen-bond activation of aldimines.

Original languageEnglish (US)
Pages (from-to)759-764
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume349
Issue number4-5
DOIs
StatePublished - Mar 1 2007

Keywords

  • Amino acids
  • BINOL phosphate
  • Brønsted acid
  • Hydrocyanation
  • Strecker reaction
  • TADDOL

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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