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

26 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

Fingerprint Dive into the research topics of 'Cross-coupling reactions between α,β-unsaturated ketones and aldehydes with CrCl<sub>2</sub>: Aldol condensation and cyclopropanol formation'. Together they form a unique fingerprint.

Cite this

@article{dc3ab77cd1db4493a49fcaa1a3550d39,

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",

month = aug,

day = "4",

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

language = "English",

volume = "39",

pages = "2725--2727",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "15",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=0034604558&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034604558&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20000804)39:15<2725::AID-ANIE2725>3.0.CO;2-U

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

M3 - Article

AN - SCOPUS:0034604558

VL - 39

SP - 2725

EP - 2727

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 15

ER -