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1,5-Induction in reactions of 4-alkoxy-2-trimethylsilylalk-2-enyl(tributyl)stannanes with aldehydes

✍ Scribed by Nicholas H Taylor; Eric J Thomas

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 759 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00442-1

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✦ Synopsis

2-Trimethylsilylalk-2-enylstannanes undergo tin(IV) chloride promoted reactions with aldehydes to give homoallylic alcohols with retention of the 2-lrimethylsilyl group. 4-Alkoxy-2-trimethylsilylalk-2-enyl(tributyl)stannane 31 reacts with aldehydes under these conditions with excellent stereoselectivity in favour of the 1,5-syn-(E)-products 32 -35. Preliminary studies into the chemistry of these vinylsilanes have been carried out.

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