Strained Silacycles in Organic Synthesis: The Tandem Aldol−Allylation Reaction
- 15 August 2002
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (36) , 10672-10673
- https://doi.org/10.1021/ja027655f
Abstract
Allyl(crotyl)enolsilanes, when constrained in a five-membered ring with a 1,2-diol, react with aldehydes in a tandem aldol−allylation reaction to give polyketide fragments. These experimentally trivial and efficient reactions establish two new carbon−carbon bonds and up to four new stereocenters. The silane reagents, which owe their reactivity to strain release Lewis acidity, are easily prepared and stable to storage.Keywords
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