Stereodivergent α-allylation of linear aldehydes with dual iridium and amine catalysis

Simon Krautwald, Michael A. Schafroth, David Sarlah, Erick M. Carreira

Research output: Contribution to journalArticlepeer-review

Abstract

We describe the fully stereodivergent, dual catalytic α-allylation of linear aldehydes. The reaction proceeds via direct iridium-catalyzed substitution of racemic allylic alcohols with enamines generated in situ. The use of an Ir(P,olefin) complex and a diarylsilyl prolinol ether as catalysts in the presence of dimethylhydrogen phosphate as the promoter proved to be crucial for achieving high enantio- and diastereoselectivity (>99% ee, up to >20:1 dr). The utility of the method is demonstrated in a concise enantioselective synthesis of the antidepressant (-)-paroxetine.

Original languageEnglish (US)
Pages (from-to)3020-3023
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number8
DOIs
StatePublished - Feb 26 2014
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Stereodivergent α-allylation of linear aldehydes with dual iridium and amine catalysis'. Together they form a unique fingerprint.

Cite this