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Synthesis of Chiral 1,4‐Benzodioxanes and Chromans by Enantioselective Palladium‐Catalyzed Alkene Aryloxyarylation Reactions
Author(s) -
Hu Naifu,
Li Ke,
Wang Zheng,
Tang Wenjun
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600379
Subject(s) - enantioselective synthesis , alkene , stereocenter , chemistry , reactivity (psychology) , steric effects , palladium , chiral ligand , ligand (biochemistry) , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , medicine , biochemistry , alternative medicine , receptor , pathology
A highly enantioselective alkene aryloxyarylation led to the high‐yielding formation of a series of 1,4‐benzodioxanes, 1,4‐benzooxazines, and chromans containing quaternary stereocenters with excellent enantioselectivity. The sterically bulky and conformationally well defined chiral monophosphorus ligand L4 or L5 was responsible for the high reactivity and enantioselectivity of these transformations. The application of this method to the synthesis of the chiral chroman backbone of α‐tocopherol was demonstrated.