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Copper‐Catalyzed Stereoselective Aminoboration of Bicyclic Alkenes
Author(s) -
Sakae Ryosuke,
Hirano Koji,
Satoh Tetsuya,
Miura Masahiro
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.201409104
Subject(s) - bicyclic molecule , stereospecificity , chemistry , amine gas treating , olefin fiber , copper , catalysis , stereoselectivity , ligand (biochemistry) , selectivity , boron , combinatorial chemistry , molecule , stereochemistry , organic chemistry , medicinal chemistry , receptor , biochemistry
A copper‐catalyzed aminoboration of bicyclic alkenes, including oxa‐ and azabenzonorbornadienes, has been developed. With this method, amine and boron moieties are simultaneously introduced at an olefin with exo selectivity. Subsequent stereospecific transformations of the boryl group can provide oxygen‐ and nitrogen‐rich cyclic molecules with motifs that may be found in natural products or pharmaceutically active compounds. Moreover, a catalytic asymmetric variant of this transformation was realized by using a copper complex with a chiral bisphosphine ligand, namely ( R , R )‐Ph‐BPE.