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 journal › Article

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

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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 journal › Article

Takai, K, Morita, R & Toratsu, C 2001, 'Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl', Angewandte Chemie - International Edition, vol. 40, no. 6, pp. 1116-1119. https://doi.org/10.1002/1521-3773(20010316)40:6<1116::AID-ANIE11160>3.0.CO;2-T
Takai K, Morita R, Toratsu C. Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl. Angewandte Chemie - International Edition. 2001 Mar 14;40(6):1116-1119. https://doi.org/10.1002/1521-3773(20010316)40:6<1116::AID-ANIE11160>3.0.CO;2-T
Takai, Kazuhiko ; Morita, Ryotaro ; Toratsu, Chika. / Stereoselective cross pinacol-type coupling between α,β-unsaturated ketones and aldehydes mediated by chromium(II) and r3SiCl. In: Angewandte Chemie - International Edition. 2001 ; Vol. 40, No. 6. pp. 1116-1119.
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