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Asymmetric Hydrogenation of In Situ Generated Isochromenylium Intermediates by Copper/Ruthenium Tandem Catalysis
Author(s) -
Miao Tingting,
Tian ZiYou,
He YanMei,
Chen Fei,
Chen Ya,
Yu ZhiXiang,
Fan QingHua
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201611291
Subject(s) - ruthenium , asymmetric hydrogenation , cationic polymerization , tandem , chemistry , catalysis , enantioselective synthesis , copper , in situ , combinatorial chemistry , diamine , organic chemistry , materials science , composite material
The first asymmetric hydrogenation of in situ generated isochromenylium derivatives is enabled by tandem catalysis with a binary system consisting of Cu(OTf) 2 and a chiral cationic ruthenium–diamine complex. A range of chiral 1 H ‐isochromenes were obtained in high yields with good to excellent enantioselectivity. These chiral 1 H ‐isochromenes could be easily transformed into isochromanes, which represent an important structural motif in natural products and biologically active compounds. The chiral induction was rationalized by density functional theory calculations.