Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl

Kazuhiko Takai, Ryotaro Morita, Chika Toratsu

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

Efficient trapping of chromium enolates in the presence of Et3SiCl gives silyl enol ethers. This trapping changes the course of the reaction between α,β-unsaturated ketones and aldehydes from a sequential aldol-cyclopropanol formation to a cross pinacol-type coupling reaction (Eq. (1); for example, R1=n-C8H17,R2=Ph(CH2) 2]. The antilsyn ratios of the 1,2-diols depend on the reaction temperature.

Original languageEnglish
Pages (from-to)1116-1119
Number of pages4
JournalAngewandte Chemie - International Edition
Volume40
Issue number6
DOIs
Publication statusPublished - Mar 14 2001

Keywords

  • Aldehydes
  • Chromium
  • Diols
  • Ketones
  • Pinacol coupling

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r<sub>3</sub>SiCl'. Together they form a unique fingerprint.

Cite this