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 journalArticle

36 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

Fingerprint

Ethers
Chromium
Ketones
Aldehydes
Temperature
cyclopropanol
3-hydroxybutanal

Keywords

  • Aldehydes
  • Chromium
  • Diols
  • Ketones
  • Pinacol coupling

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl. / Takai, Kazuhiko; Morita, Ryotaro; Toratsu, Chika.

In: Angewandte Chemie - International Edition, Vol. 40, No. 6, 14.03.2001, p. 1116-1119.

Research output: Contribution to journalArticle

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