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Abstract
The reactivity of ( E)-1-( tert-butyldimethyl)silyloxy-3,3-bis(tributylstannyl)propene 1 as potential 1,3 dianion equivalent has been investigated. Condensation with aldehydes 4a–h, in presence of BF 3·OEt 2, afforded in high yields the mono-protected diols 5a–h exhibiting an exclusive E configuration of the vinyltin residue. Good to high syn selectivities have been measured, in agreement with an S E′ addition mechanism. Further transformation of the resulting vinyltin moiety of these diols into various functionalities has been successfully tested. © 1997 Elsevier Science Ltd.
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