Abstract
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Racemic lithium tert-butyl phenylmethyl sulfoxide 1A when quenched with benzophenone gives CR*SR*-2-tert-butylsulfmyl)-1,1,2-triphenylethanol as determined by single-crystal X-ray analysis. The diastereoselection in the reaction of 1A with various aldehydes and imines as a function of aldehyde and imline structure and metal cation (Li+or Zn2+) is reported. Both substrates show a preference for anti diastereoselection. Transition-state structures are proposed to account for this diastereoselection. © 1989, American Chemical Society. All rights reserved.