Remote stereocontrol using allylstannanes: reversal in stereoselectivity using indium(iii) and bismuth(iii) halides as promoters,10.1039/B303151A

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

Sam Donnelly,Eric J. Thomas,Euan A. Arnott

Chemical Communications Pub Date : 05/20/2003 00:00:00 , 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.