New Strategy for the Asymmetric Synthesis of Phenyl Ketone Cyanohydrins: Quaternization of Cyanohydrins Derived from 2-p-Tolylsulfinyl Benzaldehyde.

Optically pure functionalized cyanohydrins derived from 1-[2-(p-tolylsulfinyl)phenyl] ethanone can be obtained by the reaction of 2-p-tolylsulfinyl benzaldehyde derived cyanohydrins with bases and further treatment with suitable electrophiles. High yields and excellent stereoselectivities (up to de »98%) were obtained for these remote 1,4-asymmetric induction processes controlled by a sulfinyl chiral inductor. [ABSTRACT FROM AUTHOR]