Stereoselective [4 + 1] Annulation Reactions with Silyl Vinylketenes Derived from Fischer Carbene Complexes

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• 作者：William H. Moser ; Laura A. Feltes ; Liangdong Sun ; Matthew W. Giese ; Ryan W. Farrell
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：August 18, 2006
• 年：2006
• 卷：71
• 期：17
• 页码：6542 - 6546
• 全文大小：101K
• 年卷期：v.71,no.17(August 18, 2006)
• ISSN：1520-6904

文摘

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Stable silyl vinylketenes were prepared via the thermal reaction of Fischer carbene complexes withtriisopropylsilyl- or tert-butyldimethylsilyl-substituted alkynes. The ability of these silyl vinylketenes toparticipate with carbenoid reagents in [4 + 1] annulation reactions was investigated. The best resultswere obtained with diazomethane and substituted diazomethane reagents, which provided cyclopentenoneproducts in excellent yields and essentially complete stereoselectivity.