Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using triphenyl- phosphoranylideneketene (the Bestmann ylide) and their use in Wittig reactions.
Camphor-derived lactams and other related chiral controllers have been found to react with the Bestmann ylide (triphenylphosphoranylideneketene) upon heating in toluene. The resulting parent ylides provide convenient access to a structurally diverse set of chiral stabilized ylides via functionalization. The utility of these chiral ylides for Wittig reactions has been briefly investigated and the effects of alpha-substitution noted.
Boeckman
Robert K
RK
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA. rkb@rkbmac.chem.rochester.edu
Song
Xinyi
X
Pero
Joseph E
JE