Synthesis of Chiral Polycyclic Tetrahydrocarbazoles by Enantioselective Aminocatalytic Double Activation of 2-Hydroxycinnamaldehydes with Dienals
Yong-Chao Ming, Xuejiao Lv, Ming Liu, Yankai Liu
Abstract
An efficient aminocatalytic enantioselective double-activation strategy has been developed that combines several different aminocatalytic modes in a cascade process, such as iminium ion, vinylogous iminium ion, trienamine, and dienamine activations. By using this strategy, 2-hydroxycinnamaldehydes worked well with various dienals via [4 + 2] cycloaddition and the oxa-Michael reaction-initiated cascade, respectively, leading to chiral polycyclic tetrahydrocarbazole and chromane derivatives with excellent diastereo- and enantioselectivities.
Topics & Concepts
IminiumChemistryEnantioselective synthesisCycloadditionCascadeCombinatorial chemistryOrganocatalysisCatalysisStereochemistryOrganic chemistryChromatographyAsymmetric Synthesis and CatalysisChemical synthesis and alkaloidsAxial and Atropisomeric Chirality Synthesis