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  • Title: Radical migration-addition of N-tert-butanesulfinyl imines with organozinc reagents.
    Author: Huang W, Ye JL, Zheng W, Dong HQ, Wei BG.
    Journal: J Org Chem; 2013 Nov 15; 78(22):11229-37. PubMed ID: 24160561.
    Abstract:
    A novel migration-addition sequence was discovered for the reaction of enantioenriched N-tert-butanesulfinyl iminoacetate 1a with functionalized benzylzinc bromide reagents, producing tert-leucine derivatives in excellent diastereoselectivity (dr 98:2). The absolute configurations of two new chiral centers were unambiguously assigned by chemical transformations and X-ray crystallography. In addition, the regio- and diastereoselectivities of this novel reaction were both explained through the key N-sulfinamine intermediate M6 generated by the tert-butyl radical attack on the imine. Computational analysis of this reaction process, which was performed at the B3LYP/6-311++G(3df,2p)//B3LYP/6-31G*-LANL2DZ level, also supported our proposed two-stage mechanism.
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