Stereoselective Synthesis Of Chiral Thiol-Containing 1,2-Aminoalcohols Via Smi2-Mediated Coupling

The stereoselective synthesis of highly functionalized aminohydroxythiols represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI2/LiBr-mediated reductive coupling between Ellman N-sulfinylimines, containing thiol groups protected either as trityl thioether or dihydrothiazolidine, and aldehydes enables the synthesis of chiral aminohydroxythiols in high enantio- and diastereoselectivity. The scope of this reaction has been established for 18 examples and applied for the synthesis of a complex intermediate needed for a biosynthesis study. (C) 2020 The Authors. Published by Elsevier Ltd.