Zinc-Catalyzed Hydroxyl-Directed Regioselective Ring Opening of Aziridines in S_N2 Reaction Pathway

In this protocol, a zinc-catalyzed catalytic regioselective ring opening of electronically and sterically unbiased 2,3-aziridinyl alcohols has been accomplished. The directing effect of the hydroxyl moiety enables the selective nucleophilic attack to the C-3 position of 2,3-aziridinyl alcohols with various aromatic amines and thiophenols as nucleophiles. This operationally simple reaction provides convenient access to a variety of amino alcohols and hydroxyl sulfides in excellent regiocontrol. Moreover, simple derivatization of the ring opening product establishes a general strategy to approach internal vicinal diamines in regioselective and diastereomerically pure form.