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Enantioselective Copper‐Catalyzed Alkylation of Quinoline N ‐Oxides with Vinylarenes
Author(s) -
Yu Songjie,
Sang Hui Leng,
Ge Shaozhong
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709411
Subject(s) - enantioselective synthesis , alkylation , quinoline , chemistry , catalysis , yield (engineering) , copper , combinatorial chemistry , alkyl , organic chemistry , materials science , metallurgy
An asymmetric copper‐catalyzed alkylation of quinoline N ‐oxides with chiral Cu–alkyl species, generated by migratory insertion of a vinylarene into a chiral Cu−H complex, is reported. A variety of quinoline N ‐oxides and vinylarenes underwent this Cu‐catalyzed enantioselective alkylation reaction, affording the corresponding chiral alkylated N‐heteroarenes in high yield with high‐to‐excellent enantioselectivity. This enantioselective protocol represents the first general and practical approach to access a wide range of chiral alkylated quinolines.