Recoverable chiral sulfoxides for asymmetric synthesis: preparation, regeneration and application to the asymmetric aldol reaction
Abstract
The synthesis of a novel source of chiral sulfoxide and its application to the control of asymmetric aldol reactions is described. The sulfoxide precursor S(s)R-(+)-cis-4 may be recycled and thus affords a considerable advantage over currently available methodology. Studies of the origin of the stereochemical outcome of the aldol reactions of the derived enolate S(s)R-(–)-10b reveal that it is the result of thermodynamic, not kinetic, control.