The First Copper-Directed Regio- and anti-Selective Vicinal Acetoxysulfenylation of Nitroalkenes Generated in situ via the Henry Reaction

摘要

The first example of a convenient, efficient, and highly regio- and anti-stereoselective multicomponent synthesis of vicinal acetoxysulfenylnitroalkanes along with the preparation of a probe for demonstrating their utility in heterocyclic synthesis is reported. The protocol strategically involves one-pot sequential Henry (ni_troaldol) reaction, dehydration, and vicinal functionalization of the olefinic bond of in situ generated nitrostyrenes. The olefinic bond undergoes copper(l)/imidazole-catalyzed vicinal acetoxysulfenyl_ation with an organodisulfide and acetic acid under air followed by reductive cyclization to afford aziridines in good yields (79-84%).