Sequential Visible-Light and <i>N</i>-Heterocyclic Carbene Catalysis: Stereoselective Synthesis of Tetrahydropyrano[2,3-<i>b</i>]indoles
Chengyuan Wang, Zheyuan Wang, Jin Yang, Shi‐Hui Shi, Xin‐Ping Hui
Abstract
An efficiently stereoselective [4 + 2] cycloaddition of 3-alkylenyloxindoles and α-diazoketones through sequential visible-light photoactivation and N-heterocyclic carbene catalysis was achieved. A series of tetrahydropyrano[2,3-b]indoles with an all-carbon quaternary stereocenter were obtained in good yields with excellent diastereo- and enantioselectivities.
Topics & Concepts
CarbeneStereocenterChemistryStereoselectivityCatalysisCycloadditionCombinatorial chemistryStereochemistryOrganic chemistryEnantioselective synthesisN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms