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Enantioselective Copper‐Catalyzed Allylic Substitution Reaction with Aminohydroxyphosphine Ligand
Author(s) -
Yoshikai Naohiko,
Miura Kotaro,
Nakamura Eiichi
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900054
Subject(s) - chemistry , allylic rearrangement , enantioselective synthesis , copper , ligand (biochemistry) , olefin fiber , catalysis , zinc , medicinal chemistry , substitution reaction , substitution (logic) , stereochemistry , proline , organic chemistry , amino acid , receptor , biochemistry , computer science , programming language
AbstractA proline‐derived aminohydroxyphosphine ligand induced excellent regio‐ and enantioselectivities (S N 2′:S N 2>94:6, 94–97% ee ) in the copper‐catalyzed substitution reaction of cinnamyl phosphates with Et 2 Zn. A computational modelling study of the reaction pathway suggests that the displacement of the leaving group takes place in an ordered, anti ‐fashion through simultaneous copper–olefin and zinc–oxygen interactions, which is critical for the enantioselection.