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The asymmetric ketone-tert-butanesulfinyl (t-BS) imine pinacol-type reductive coupling promoted by SmI(2) is described. Trans-1,2-vicinal amino alcohols were formed predominantly in excellent er and high dr. The stereochemical outcome provided evidence for a radical mechanism for SmI(2)-induced reductive couplings of t-BS imines.
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Wang et al. (2009) studied this question.
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