Diastereoselective Synthesis of Seven-Membered-Ring trans-Alkenes from Dienes and Aldehydes by Silylene Transfer

Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigm...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-08, Vol.134 (30), p.12482-12484
Main Authors: Greene, Margaret A, Prévost, Michel, Tolopilo, Joshua, Woerpel, K. A
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Alkenes - chemical synthesis
Alkenes - chemistry
Catalysis
Polyenes - chemical synthesis
Polyenes - chemistry
Silanes - chemical synthesis
Silanes - chemistry
Silver - chemistry
Stereoisomerism
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Summary:Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen–hydrogen bonds across the carbon–carbon double bonds.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja305713v