Organocatalytic Asymmetric (4 + 3) Cycloaddition toward Optically Active Cyclohepta Fused Diindoles
Kanghua Rui, Hanxiao Shen, Xufeng Lin
Abstract
A novel asymmetric (4 + 3) cycloaddition of indole-2,3-quinodimethanes in situ generated from 3-methyl-2-indolylmethanols with 3-indolylmethanols via chiral phosphoric acid catalysis has been established. The cycloaddition reaction exhibits a broad substrate scope affording the diverse enantioenriched cyclohepta fused diindoles in high yields with good enantioselectivities. Significantly, this work represents the first application of 3-methyl-2-indolylmethanols as 4C synthons instead of the commonly reported three-atom synthons in cycloaddition reactions.
Topics & Concepts
Optically activeCycloadditionEnantioselective synthesisChemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalysisAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacology