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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Strained silacycles in organic synthesis: the tandem aldol-allylation reaction
Xiaolun Wang1, Qinglin Meng, Andrew J Nation
1Department of Chemistry, Columbia University, New York, NY 10027, USA.
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.
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