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Palladium‐Catalyzed Asymmetric Amination of Allenyl Phosphates: Enantioselective Synthesis of Allenes with an Additional Unsaturated Unit
Author(s) -
Li Qiankun,
Fu Chunling,
Ma Shengming
Publication year - 2014
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.201402647
Subject(s) - enantioselective synthesis , amination , palladium , yield (engineering) , catalysis , ligand (biochemistry) , allene , chemistry , axial chirality , organic chemistry , chirality (physics) , medicinal chemistry , combinatorial chemistry , materials science , physics , nambu–jona lasinio model , biochemistry , receptor , metallurgy , chiral symmetry breaking , quantum mechanics , quark
Abstract A highly enantioselective Pd‐catalyzed amination of allenyl phosphates generating 2,3‐allenyl amines with central chirality has been developed. Under the optimized conditions, chiral 2,3‐allenyl amines with or without (an) additional CC double or triple bond(s) have been prepared at 0 °C with up to 90 % yield and 94 % ee by identifying ( R )‐3,4,5‐(MeO) 3 ‐MeOBIPHEP as the ligand.