Highly Diastereoselective and Enantioselective Synthesis of Enantiopure <i>C</i>₂-Symmetrical Vicinal Diamines by Reductive Homocoupling of Chiral <i>N-tert-</i>Butanesulfinyl Imines

Abstract

[reaction: see text] An efficient and straightforward method for the preparation of highly enantiomerically enriched C2-symmetrical vicinal diamines by the reductive homocoupling of aromatic N-tert-butanesulfinyl imines in the presence of SmI2 and HMPA was developed. It gives access to a variety of enantiopure C2-symmetrical 1,2-diamines in a very mild and practical way.