Enantioselective Generation of Benzylic Stereocenters Mediated by a Remote Sulfoxide

Abstract

ortho-Sulfinyl-substituted benzyllithium reagents react with aldehydes and ketones to afford, after desulfurization with Raney-Nickel, stereoselective access to benzylic stereocenters [Eq. (1)]. This is the first efficient asymmetric 1,4-induction with mediation by a sulfoxide group. LDA=lithium diisopropylamide; Tol=tolyl; TIPS=triisopropylsilyl. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2000/z14652_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.