Issue 19, 2002
From the journal:

Chemical Communications

First anionic silyl migration from sp2 carbon to carbonyl oxygen. Stereospecific allylation of (Z)-β-trimethylsilyl-α,β-unsaturated ketones

Haruhiko Taguchi,a   Hiroko Miyashita,a   Akira Tsubouchia  and  Takeshi Takeda*a  

* Corresponding authors

a Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan
E-mail: takeda-t@cc.tuat.ac.jp
Fax: +81 42 388 7034
Tel: +81 42 388 7034

Abstract

1,4-Silyl migration from sp2 carbon to carbonyl oxygen proceeded by the treatment of (Z)-β-trimethylsilyl-α,β-unsaturated ketones with copper(I) tert-alkoxide to afford vinylmetal species, which reacted with allylic halides to produce enol trimethylsilyl ethers of β-alk-2-enyl-α,β-unsaturated ketones with complete retention of configuration.

Graphical abstract: First anionic silyl migration from sp2 carbon to carbonyl oxygen. Stereospecific allylation of (Z)-β-trimethylsilyl-α,β-unsaturated ketones

About
Cited by
Related
Download options Please wait...

Additions and corrections

Article information

DOI
https://doi.org/10.1039/B207325K
Article type
Communication
Submitted
25 Jul 2002
Accepted
20 Aug 2002
First published
05 Sep 2002

Chem. Commun., 2002, 2218-2219

Permissions

Request permissions

First anionic silyl migration from sp2 carbon to carbonyl oxygen. Stereospecific allylation of (Z)-β-trimethylsilyl-α,β-unsaturated ketones

H. Taguchi, H. Miyashita, A. Tsubouchi and T. Takeda, Chem. Commun., 2002, 2218 DOI: 10.1039/B207325K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements