General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation
Priscilla Mendonça Matos, William Lewis, Stephen P. Argent, Jonathan C. Moore, Robert A. Stockman
Abstract
A 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.
Topics & Concepts
ChemistryYield (engineering)ReagentArylAlkylCombinatorial chemistryTemplateRing (chemistry)Organic chemistryNanotechnologyMetallurgyMaterials scienceSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques