Stereoselective [4 + 1] annulation reactions with silyl vinylketenes derived from Fischer carbene complexes.
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.
Moser
William H
WH
Department of Chemistry, Indiana University-Purdue University Indianapolis, Indianapolis, Indiana 46202, USA. wmoser@mmm.com
Feltes
Laura A
LA
Sun
Liangdong
L
Giese
Matthew W
MW
Farrell
Ryan W
RW