Advantage of in situ Generation of N-Arylsulfonyl Imines from α-Amide Sulfones in the Phase Transfer Catalyzed Asymmetric Strecker Reaction.

Abstract Highly efficient, catalytic enantioselective synthesis of N -arylsulfonyl α-amino nitriles from the corresponding α-amido sulfones has been achieved under toluene–aqueous potassium cyanide biphasic conditions using chiral quaternary ammonium iodide ( R , R , R )- 1 as an effective phase-transfer catalyst. This Strecker synthesis involving the in situ generation of the reactive N -sulfonyl imines is advantageous for the cyanation of the substrates having primary and secondary alkyl substituents.