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Divergent stereochemical outcomes in the insertion of donor/donor carbenes into the C–H bonds of stereogenic centers

Sarah N. Dishman, Croix J. Laconsay, James C. Fettinger, Dean J. Tantillo, Jared T. Shaw

2021Chemical Science16 citationsDOIOpen Access PDF

Abstract

2 mechanism that is either controlled by the substrate or the catalyst. These results demonstrate that donor/donor carbenes undergo uniquely stereoselective reactions that originate from a stepwise reaction mechanism, in contrast to the analogous concerted reactions of carbenes with one or more electron-withdrawing groups attached.

Topics & Concepts

StereocenterChemistryStereochemistryEnantioselective synthesisOrganic chemistryCatalysisCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions