Issue 12, 2003

Remote stereocontrol using allylstannanes: reversal in stereoselectivity using indium(iii) and bismuth(iii) halides as promoters

Abstract

Allyl-indium(III) and -bismuth(III) dihalides, generated by transmetallation of 5-benzyloxy-4-methylpent-2-enyl(tributyl)stannane 1, react with aldehydes with useful levels of 1,5-stereocontrol, a 93 ∶7 ratio of 1,5-epimers in favour of the 1,5-anti-(E)-stereoisomers 7 and 11 typically being obtained using bismuth(III) iodide. The 4-benzyloxypent-2-enylstannane 4 similarly gives the 1,5-syn-(E)-hex-3-enols 13 also with ca. 93 ∶7, stereoselectivity.

Graphical abstract: Remote stereocontrol using allylstannanes: reversal in stereoselectivity using indium(iii) and bismuth(iii) halides as promoters

Article information

Article type
Communication
Submitted
19 Mar 2003
Accepted
01 May 2003
First published
20 May 2003

Chem. Commun., 2003, 1460-1461

Remote stereocontrol using allylstannanes: reversal in stereoselectivity using indium(III) and bismuth(III) halides as promoters

S. Donnelly, E. J. Thomas and E. A. Arnott, Chem. Commun., 2003, 1460 DOI: 10.1039/B303151A

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