American Chemical Society
ja3013825_si_003.cif (14.56 kB)

Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines

Download (14.56 kB)
posted on 2012-06-13, 00:00 authored by Chung-Yang (Dennis) Huang, Abigail G. Doyle
A nickel-catalyzed cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is reported. The catalytic system comprises an inexpensive and air-stable Ni­(II) source and dimethyl fumarate as ligand. Regioselective synthesis of β-substituted amines is possible under mild and functional-group-tolerant conditions. The stereoselectivity of the reaction is consistent with a stereoconvergent mechanism wherein the sulfonamide directs C–C bond formation.