H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins
Peigang Ding, Feng Zhou, Xin Wang, Qiuhua Zhao, Jin‐Sheng Yu, Jian Zhou
Abstract
We report the successful reversal of the diastereoselectivity in an unprecedented Michael addition of α-azido ketones to nitroolefins catalyzed by bifunctional tertiary amines, simply by varying the H-bond donor from phosphoramide to squaramide.
Topics & Concepts
SquaramideBifunctionalMichael reactionChemistryCombinatorial chemistryStereochemistryOrganic chemistryOrganocatalysisCatalysisEnantioselective synthesisSynthesis and Catalytic ReactionsAsymmetric Synthesis and CatalysisChemical Synthesis and Analysis