STEREOSELECTIVE ADDITION-REACTIONS OF CHIRAL N-BENZYLIDENE-PARA-TOLUENESULFINAMIDES - ASYMMETRIC SYNTHESES OF BETA-AMINO AND GAMMA-AMINO ACIDS

Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitrile with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate. Treatment of 2 with allylmagnesium bromide in ether at 0-degrees-C gave the adducts (R)-7 with excellent stereoselectivity. Pure chiral sulfinamides 7 were converted into chiral beta- and gamma-amino acids in four and five steps, respectively.