Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)AlIII

Christopher R. Graves, Karl A. Scheidt*, Son Binh T. Nguyen

*Corresponding author for this work

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)AlIII/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.

Original languageEnglish (US)
Pages (from-to)1229-1232
Number of pages4
JournalOrganic Letters
Volume8
Issue number6
DOIs
StatePublished - Mar 16 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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