Cross-pinacol-type coupling reactions between α,β-unsaturated ketones and aldehydes with low-valent metals

Kazuhiko Takai, Ryotaro Morita, Hiroshi Matsushita, Chika Toratsu

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Treatment of an α,β-unsaturated ketone and an aldehyde with chromium (II) chloride and R3SiCl in DMF gives cross-pinacol-type coupling products, 1,2-diols selectively. The anti/syn ratios of the produced 1,2-diols are shown to depend on the reaction temperature: At lower temperatures, the anti adduct is produced selectively, but at higher temperatures, the anti/syn ratios gradually decrease. When a combination of manganese and a catalytic amount of lead are used instead of chromium(II), 1,6-diketone, a dimer of the α,β-unsaturated ketone, is produced selectively.

Original languageEnglish
Pages (from-to)17-23
Number of pages7
JournalChirality
Volume15
Issue number1
DOIs
Publication statusPublished - 2003

Fingerprint

Ketones
Aldehydes
Metals
Chromium
Temperature
Manganese
Dimers
Chlorides
Lead

Keywords

  • 1,2-diol
  • Chromium
  • Manganese
  • Pinacol-coupling
  • Synthetic methods

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Cross-pinacol-type coupling reactions between α,β-unsaturated ketones and aldehydes with low-valent metals. / Takai, Kazuhiko; Morita, Ryotaro; Matsushita, Hiroshi; Toratsu, Chika.

In: Chirality, Vol. 15, No. 1, 2003, p. 17-23.

Research output: Contribution to journalArticle

Takai, Kazuhiko ; Morita, Ryotaro ; Matsushita, Hiroshi ; Toratsu, Chika. / Cross-pinacol-type coupling reactions between α,β-unsaturated ketones and aldehydes with low-valent metals. In: Chirality. 2003 ; Vol. 15, No. 1. pp. 17-23.
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