Rh(II)-Catalyzed Enantioselective <i>S</i>-Alkylation of Sulfenamides with Acceptor–Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality
Shivani Patel, Nathaniel S. Greenwood, Brandon Q. Mercado, Jonathan A. Ellman
Abstract
The Rh(II)-catalyzed enantioselective S -alkylation of sulfenamides with α-amide diazoacetates at 1 mol % catalyst loading to obtain sulfilimines in high yields and enantiomeric ratios of up to 99:1 is reported. The enantioenriched sulfilimine products incorporate versatile amide functionality poised for further elaboration to diverse sulfoximines with multiple stereogenic centers, including by highly diastereoselective sulfilimine and sulfoximine α-alkylation with alkylating agents and epoxides and by interconversion of the amide to N - tert -butanesulfinyl aldimines, followed by diastereoselective additions.
Topics & Concepts
DiazoEnantioselective synthesisChemistryAcceptorCatalysisAlkylationCombinatorial chemistryOrganic chemistryStereochemistryPhysicsCondensed matter physicsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms