Strained silacycles in organic synthesis: the tandem aldol-allylation reaction |
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Authors: | Wang Xiaolun Meng Qinglin Nation Andrew J Leighton James L |
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Institution: | Department of Chemistry, Columbia University, New York, NY 10027, USA. |
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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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