Premium
Pd‐Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction
Author(s) -
Cheng Qiang,
Xie JiaHao,
Weng YueCheng,
You ShuLi
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901251
Subject(s) - borane , chemistry , catalysis , activator (genetics) , reactivity (psychology) , combinatorial chemistry , enantioselective synthesis , ligand (biochemistry) , medicinal chemistry , organic chemistry , receptor , medicine , biochemistry , alternative medicine , pathology
Dearomatization of anthranils with vinylcyclopropanes (VCPs) by Pd‐catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introducing a chiral PHOX ligand ( L5 ), asymmetric dearomatization reactions of anthranils with vinylcyclopropanes proceeded with excellent enantioselectivity. Borane plays a key role for the reactivity, likely owing to the formation of a borane–anthranil complex which has been confirmed by NMR experiments.