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

Kazuhiko Takai; Ryotaro Morita; Hiroshi Matsushita; Chika Toratsu

doi:10.1002/chir.10148

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 journal › Article › peer-review

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 language	English
Pages (from-to)	17-23
Number of pages	7
Journal	Chirality
Volume	15
Issue number	1
DOIs	https://doi.org/10.1002/chir.10148
Publication status	Published - Jan 1 2003

Keywords

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

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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

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.",

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AU - Takai, Kazuhiko

AU - Morita, Ryotaro

AU - Matsushita, Hiroshi

AU - Toratsu, Chika

PY - 2003/1/1

Y1 - 2003/1/1

N2 - 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.

AB - 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.

KW - 1,2-diol

KW - Chromium

KW - Manganese

KW - Pinacol-coupling

KW - Synthetic methods

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

Abstract

Keywords

ASJC Scopus subject areas

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