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Cationic Iridium/S‐Me‐BIPAM‐Catalyzed Direct Asymmetric Intermolecular Hydroarylation of Bicycloalkenes
Author(s) -
Shirai Tomohiko,
Yamamoto Yasunori
Publication year - 2015
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.201504563
Subject(s) - enantioselective synthesis , cationic polymerization , chemistry , acetophenone , norbornene , iridium , catalysis , benzamide , alkylation , phosphoramidite , medicinal chemistry , chiral ligand , bond cleavage , polymer chemistry , organic chemistry , copolymer , polymer , dna , biochemistry , oligonucleotide
Highly enantioselective cationic iridium‐catalyzed hydroarylation of bicycloalkenes, by carbonyl‐directed CH bond cleavage, was accomplished using a newly synthesized sulfur‐linked bis(phosphoramidite) ligand (S‐Me‐BIPAM). The reaction provides alkylated acetophenone or benzamide derivatives in moderate to excellent yields and good to excellent enantioselectivities. Notably, the hydroarylation reaction of 2‐norbornene with N , N ‐dialkylbenzamide proceeds with excellent enantioselectivity (up to 99 % ee ) and high selectivity for the mono‐ ortho ‐alkylation product.