Asymmetric 1,4-addition of alkenylzirconium reagents to α,β-unsaturated ketones catalyzed by chiral rhodium complexes

Shuichi Oi, Takashi Sato, Yoshio Inoue

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Highly enantioselective 1,4-addition of alkenylzirconocene chlorides to α,β-enones was found to be catalyzed by a chiral rhodium complex generated from [Rh(cod)(MeCN)2]BF4 and (S)-BINAP. The reaction can be applied to either cyclic or acyclic enones and the optical yield was up to 99% ee. The reaction mechanism would involve the transmetalation between the alkenylzirconocene chloride and the rhodium complex to give the alkenylrhodium species as a key intermediate.

Original languageEnglish
Pages (from-to)5051-5055
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number26
DOIs
Publication statusPublished - 2004 Jun 21

Keywords

  • Alkenylzirconium
  • Asymmetric 1,4-addition
  • Rhodium catalyst
  • α,β-Enone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Asymmetric 1,4-addition of alkenylzirconium reagents to α,β-unsaturated ketones catalyzed by chiral rhodium complexes'. Together they form a unique fingerprint.

  • Cite this