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1,5-Asymmetric induction in reactions betweenδ-alkoxyallylstannanes and aldehydes induced by tin (IV) chloride

✍ Scribed by Alan H. McNeill; Eric J. Thomas

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
245 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 alcohols, both on heating and in the presence of Lewis acids,l e.g. 1-alkoxybut-2-enyl(tributyl)stannane ( 1) reacts with aldehydes at 120-140 OC to give the anti, cis-enol ethers (2), although the reaction is effectively limited to aromatic and secondary ahphatic aldehydes because of the high temperatures required.2 d-Alkoxyallylstannanes have been found to show modest diastereofacial selectivity on heating with aldehydes, e.g. (S)-4-benzyloxypent-(2E)-2-enyl(tributyl)stannane

📜 SIMILAR VOLUMES

Remote asymmetric induction in reactions
Remote asymmetric induction in reactions of 5-alkoxyalk-2-enylsilanes and aldehydes promoted by tin(IV) chloride
✍ Christopher T. Brain; Eric J. Thomas 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 286 KB

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.