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N‐Heterocyclic Carbene‐Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C−N Axial Chirality
Author(s) -
Li Tingting,
Mou Chengli,
Qi Puying,
Peng Xiaolin,
Jiang Shichun,
Hao Gefei,
Xue Wei,
Yang Song,
Hao Lin,
Chi Yonggui Robin,
Jin Zhichao
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202010606
Subject(s) - annulation , axial chirality , thiazine , carbene , catalysis , chemistry , chirality (physics) , cycloaddition , derivative (finance) , combinatorial chemistry , medicinal chemistry , axial symmetry , stereochemistry , organic chemistry , enantioselective synthesis , physics , chiral symmetry breaking , quantum mechanics , quark , financial economics , nambu–jona lasinio model , economics
Abstract A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC‐catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C−N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations.