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

Sam Donnelly; Eric J Thomas; Euan A Arnott

doi:10.1039/b303151a

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

Chem Commun (Camb). 2003 Jun 21:(12):1460-1. doi: 10.1039/b303151a.

Authors

Sam Donnelly¹, Eric J Thomas, Euan A Arnott

Affiliation

¹ Department of Chemistry, The University of Manchester, Oxford Road, Manchester, UK M13 9PL.

PMID: 12841291
DOI: 10.1039/b303151a

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.