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Remote asymmetric induction in reactions of 5-alkoxyalk-2-enylsilanes and aldehydes promoted by tin(IV) chloride

✍ Scribed by Christopher T. Brain; Eric J. Thomas

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
286 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Following observations on remote asymmetic induction using allylstannanes, 5-benzyloxy4 methylpent-2-enylsilanes are also found to react with aldebydes with modest levels of l,%induction after treatment with tin(IV) chloride. Transmetallation to give intermediite ally& hihalides may be involved.

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1,5-Asymmetric induction in reactions betweenΞ΄-alkoxyallylstannanes and aldehydes induced by tin (IV) chloride
✍ Alan H. McNeill; Eric J. Thomas πŸ“‚ Article πŸ“… 1990 πŸ› Elsevier Science 🌐 French βš– 245 KB

## Treatment of (S)-4-benzyloxypent-(2E)-enyl(tributyl)stannane (3) with tin (IV) chloride at -78 OC, followed by the addition of an aldehyde, gives Ij-diol derivatives (6) with excellent 1 J-diastereoselectiviry. Allylstannanes undergo stereoselective reactions with aldehydes to give homoahylic a