Zinc metal-promoted stereoselective olefination of aldehydes and ketones with gem-dichloro compounds in the presence of chlorotrimethylsilane | Health & Environmental Research Online (HERO)

Health & Environmental Research Online (HERO)

Print Feedback Export to File

This record has one attached file:

Citation
Tags

HERO ID

6599201

Reference Type

Journal Article

Title

Zinc metal-promoted stereoselective olefination of aldehydes and ketones with gem-dichloro compounds in the presence of chlorotrimethylsilane

Author(s)

Ishino, Y; Mihara, M; Nishihama, S; Nishiguchi, I; ,

Year

1998

Is Peer Reviewed?

Yes

Journal

Bulletin of the Chemical Society of Japan
ISSN: 0009-2673
EISSN: 1348-0634

Publisher

CHEMICAL SOC JAPAN

Location

TOKYO

Volume

Issue

Page Numbers

2669-2672

Language

English

DOI

10.1246/bcsj.71.2669

Web of Science Id

WOS:000077483400021

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0031733702&doi=10.1246%2fbcsj.71.2669&partnerID=40&md5=46580a0432576429d7879d65126d5080
Exit

Abstract

A combination of zinc metal and a catalytic amount of chlorotrimethylsilane has been found to promote the transformation of various aldehydes and ketones with gem-dichloro compounds, such as benzylidene dichloride (la) and methyl dichloroacetate (Ib), to the corresponding cross-coupling products, such as substituted styrene 3 and methyl acrylates 4 derivatives, under mild reaction conditions in THF. The E-isomer of the corresponding alkenes was obtained stereoselectively in good-to-excellent yields. The reaction serves as a very convenient one-pot procedure.