1,6-Remote stereocontrol using allylgermanes

Transmetallation of 5-hydroxy- and 5-methoxyhex-2-enyl(triethyl)germanes 8 and 9 with tin(IV) bromide is stereoselective and generates allyltin tribromides, which react with aldehydes to give (3 Z)-homoallylic alcohols 3 with useful levels of 1,6- syn-stereocontrol.

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Bibliographic Details
Published in:Tetrahedron letters 2007-01, Vol.48 (3), p.341-343
Main Authors: Thomas, Eric J., Weston, Anna P.
Format: Article
Language:English
Subjects:
Allylmetal
Diastereoselectivity
Organogermanium
Remote stereocontrol
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Description
Summary:Transmetallation of 5-hydroxy- and 5-methoxyhex-2-enyl(triethyl)germanes 8 and 9 with tin(IV) bromide is stereoselective and generates allyltin tribromides, which react with aldehydes to give (3 Z)-homoallylic alcohols 3 with useful levels of 1,6- syn-stereocontrol.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.11.070