Litcius/Paper detail

Cobalt‐Catalyzed Diastereo‐ and Enantioselective Hydroalkylation of Cyclopropenes with Cobalt Homoenolates

Wei Huang, Fanke Meng

2020Angewandte Chemie International Edition95 citationsDOI

Abstract

Catalylic diastereo- and enantioselective hydroalkylation of 3,3-disubstituted cyclopropenes with Co-homoenolate generated in situ from ring-opening of easily accessible cyclopropanols promoted by a chiral phosphine-cobalt complex is presented. Such a process represents the unprecedented and direct introduction of a wide range of functionalized alkyl groups without the need of pre-formation of stoichiometric amounts of organometallic reagents onto the cyclopropane motif, affording multi-substituted cyclopropanes in up to 99 % yield with >95:5 dr and 98:2 er. Functionalization of the products delivered enantioenriched cyclopropanes that are otherwise difficult to access.

Topics & Concepts

Enantioselective synthesisCobaltCyclopropaneCatalysisPhosphineChemistryReagentCombinatorial chemistryYield (engineering)AlkylOrganic chemistryRing (chemistry)Materials scienceMetallurgyCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods