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.