Highly stereoselective 1,4-asymmetric reactions of 2-(arylsulfinyl)benzaldehydes and 2-(arylsulfinyl)phenyl ketones

The Grignard reaction of 2-(arylsulfinyl)benzaldehydes and the DIBAL reduction of 2-(arylsulfinyl)phenyl ketones were examined. The sterically bulky (2,4,6-trimethylphenyl)- and (2,4,6-triisopropylphenyl)sulfinyl groups were shown to effect high 1,4-remote asymmetric induction. The optically active 1-phenyl-1-p-tolylmethanol could be efficiently prepared by desulfinylation of the Grignard reaction product obtained from chiral [(2,4,6-triisopropylphenyl)sulfinyl]benzaldehyde.