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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.
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Ruano et al. (2000) studied this question.
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