Cross-coupling reactions between α,β-unsaturated ketones and aldehydes with CrCl2: Aldol condensation and cyclopropanol formation

Chika Toratsu; Takafumi Fujii; Takuma Suzuki; Kazuhiko Takai

doi:10.1002/1521-3773(20000804)39:15<2725::AID-ANIE2725>3.0.CO;2-U

Cross-coupling reactions between α,β-unsaturated ketones and aldehydes with CrCl₂: Aldol condensation and cyclopropanol formation

Chika Toratsu, Takafumi Fujii, Takuma Suzuki, Kazuhiko Takai

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

Abstract

In an aprotic solvent, dimethylformamide, a coupling reaction between an α,β-unsaturated ketone and an aldehyde is achieved with chromium(II) chloride. An intermolecular aldol reaction and an intramolecular cyclization proceed sequentially to give cis-2-hydroxyalkyl-substituted cyclopropanol stereoselectively [Eq. (a)].

Original language	English
Pages (from-to)	2725-2727
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	15
DOIs	https://doi.org/10.1002/1521-3773(20000804)39:15<2725::AID-ANIE2725>3.0.CO;2-U
Publication status	Published - Aug 4 2000

Keywords

Aldehydes
Aldol reactions
Chromium
Cross-coupling
Ketones

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/1521-3773(20000804)39:15<2725::AID-ANIE2725>3.0.CO;2-U

Cite this

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title = "Cross-coupling reactions between α,β-unsaturated ketones and aldehydes with CrCl2: Aldol condensation and cyclopropanol formation",

abstract = "In an aprotic solvent, dimethylformamide, a coupling reaction between an α,β-unsaturated ketone and an aldehyde is achieved with chromium(II) chloride. An intermolecular aldol reaction and an intramolecular cyclization proceed sequentially to give cis-2-hydroxyalkyl-substituted cyclopropanol stereoselectively [Eq. (a)].",

keywords = "Aldehydes, Aldol reactions, Chromium, Cross-coupling, Ketones",

author = "Chika Toratsu and Takafumi Fujii and Takuma Suzuki and Kazuhiko Takai",

year = "2000",

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T1 - Cross-coupling reactions between α,β-unsaturated ketones and aldehydes with CrCl2

T2 - Aldol condensation and cyclopropanol formation

AU - Toratsu, Chika

AU - Fujii, Takafumi

AU - Suzuki, Takuma

AU - Takai, Kazuhiko

PY - 2000/8/4

Y1 - 2000/8/4

N2 - In an aprotic solvent, dimethylformamide, a coupling reaction between an α,β-unsaturated ketone and an aldehyde is achieved with chromium(II) chloride. An intermolecular aldol reaction and an intramolecular cyclization proceed sequentially to give cis-2-hydroxyalkyl-substituted cyclopropanol stereoselectively [Eq. (a)].

AB - In an aprotic solvent, dimethylformamide, a coupling reaction between an α,β-unsaturated ketone and an aldehyde is achieved with chromium(II) chloride. An intermolecular aldol reaction and an intramolecular cyclization proceed sequentially to give cis-2-hydroxyalkyl-substituted cyclopropanol stereoselectively [Eq. (a)].

KW - Aldehydes

KW - Aldol reactions

KW - Chromium

KW - Cross-coupling

KW - Ketones

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