Organocatalytic Asymmetric Construction of Tetrasubstituted Carbon Stereocenters Bearing Three Heteroatoms via Intramolecular Cyclization of Vinylidene ortho-Quinone Methide with Imidates

We report herein an organocatalytic asymmetric protocol for the construction of tetrasubstituted carbon stereocenters bearing three heteroatoms. The reaction proceeded via the enantioselective intramolecular cyclization reaction of vinylidene ortho-quinone methide (VQM) with imidates to form pentacy...

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Bibliographic Details
Published in:Organic letters 2022-07, Vol.24 (28), p.5073-5077
Main Authors: Tian, Yuhong, Wu, Fengdi, Jia, Shiqi, Gong, Xiangnan, Mao, Hui, Wang, Pengfei, Qin, Wenling, Yan, Hailong
Format: Article
Language:English
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Summary:We report herein an organocatalytic asymmetric protocol for the construction of tetrasubstituted carbon stereocenters bearing three heteroatoms. The reaction proceeded via the enantioselective intramolecular cyclization reaction of vinylidene ortho-quinone methide (VQM) with imidates to form pentacyclic heterocycles. The formed tetrasubstituted carbon center was stable under a high temperature and the conditions for further transformations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01842