Stereocontrolled reactions mediated by remote sulfoxides: Formation and reactivity of enantiomerically pure benzylic centers

Abstract

Reactions of different electrophiles (alkyl halides, aldehydes, N-sulfinylimines, imines, etc) with (S)-2-p-toluenesulfinyl toluene and their alkyl, triisopropylsilyloxy, and methylthio derivatives at benzylic position, in the presence of LDA, allow the synthesis of a variety of enantiomerically pure benzylic centers, whose configuration is efficiently controlled by the γ -sulfinyl group, according to 1,4-asymmetric induction processes. With prochiral electrophiles, the 1,5-asymmetric induction processes can also be controlled either by modifying their steric or electronic features or by incorporating an additional chiral center at the electrophiles. C 2007 Wiley Periodicals, Inc.