Enantioselective Cobalt‐Catalyzed Intermolecular Hydroacylation of 1,6‐Enynes
Andrew Whyte, Jonathan Bajohr, Alexa Torelli, Mark Lautens
Abstract
We report a cobalt-catalyzed hydroacylation of 1,6-enynes with exogenous aldehydes in a domino sequence to construct enantioenriched ketones. The products were obtained in good yields with excellent regio-, diastereo-, and enantioselectivity. Furthermore, the chiral products served as valuable precursors to access complex spirocyclic scaffolds with three contiguous stereocenters. The asymmetric hydroacylation process exhibited no C-H crossover and no KIE, thus indicating that the C-H bond cleavage was not involved in the turnover-limiting step.
Topics & Concepts
HydroacylationEnantioselective synthesisStereocenterDominoChemistryCobaltCatalysisStereochemistryBond cleavageIntermolecular forceCombinatorial chemistryOrganic chemistryMoleculeAldehydeCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis