American Chemical Society
ol2c01794_si_001.pdf (10.02 MB)

Organocatalytic Enantioselective 1,10-Addition of Alkynyl Indole Imine Methides with Thiazolones: An Access to Axially Chiral Tetrasubstituted Allenes

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journal contribution
posted on 2022-06-30, 11:35 authored by Xiao Lin, Boming Shen, Ziyang Wang, Yuyu Cheng, Xuling Chen, Pengfei Li, Peiyuan Yu, Wenjun Li
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.