Organocatalytic Enantioselective 1,10-Addition of Alkynyl Indole Imine Methides with Thiazolones: An Access to Axially Chiral Tetrasubstituted Allenes
Xiao Lin, Boming Shen, Ziyang Wang, Yuyu Cheng, Xuling Chen, Pengfei Li, Peiyuan Yu, Wenjun Li
Abstract
An asymmetric organocatalytic remote 1,10-addition of alkynyl indole imine methides generated in situ from α-(6-indolyl) propargylic alcohols with thiazolones has been developed for the first time, affording axially chiral tetrasubstituted allenes featuring vicinal sulfur-containing quaternary carbon stereocenters in high yields with excellent stereoselectivities. The representative scale-up reaction and transformations of the 1,10-adduct were examined. The reaction mechanism was expounded by control experiments and DFT calculations.
Topics & Concepts
StereocenterChemistryImineEnantioselective synthesisVicinalAdductIndole testOrganocatalysisCombinatorial chemistryAsymmetric carbonCatalysisOrganic chemistryStereochemistryOptically activeAxial and Atropisomeric Chirality SynthesisSynthesis of Indole DerivativesAsymmetric Synthesis and Catalysis