Journal of Organic Chemistry 2006-08-18

Stereoselective [4 + 1] annulation reactions with silyl vinylketenes derived from Fischer carbene complexes.

William H Moser, Laura A Feltes, Liangdong Sun, Matthew W Giese, Ryan W Farrell

Index: J. Org. Chem. 71 , 6542, (2006)

Full Text: HTML

Abstract

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