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General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation
Version 2 2020-03-18, 14:39
Version 1 2020-03-16, 18:34
journal contribution
posted on 2020-03-18, 14:39 authored by Priscilla Mendonça Matos, William Lewis, Stephen P. Argent, Jonathan C. Moore, Robert A. StockmanA versatile method for the synthesis
of enantioenriched N–H
sulfoximines is reported. The approach stems from the organomagnesium-mediated
ring opening of novel cyclic sulfonimidate templates. The reactions
proceed in high yield and with excellent stereofidelity with alkyl,
aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily
removed from the resultant sulfoximines via an unusual oxidative debenzylation
protocol that utilizes molecular oxygen as the terminal oxidant. This
provides a general strategy for the synthesis of highly enantioenriched
N–H sulfoximines.