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Peptidic Amidomonophosphane Ligand for Copper‐Catalyzed Asymmetric Conjugate Addition of Diorganozincs to Cycloalkenones
Author(s) -
Soeta Takahiro,
Selim Khalid,
Kuriyama Masami,
Tomioka Kiyoshi
Publication year - 2007
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.200600562
Subject(s) - chemistry , conjugate , pyrrolidine , copper , dipeptide , catalysis , enantioselective synthesis , reagent , ligand (biochemistry) , alkylation , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , amino acid , receptor , mathematical analysis , biochemistry , mathematics
Abstract Peptidic modification of ( S )‐2‐[(diphenylphosphino)methyl]pyrrolidine gave a dipeptide‐connected amidomonophosphane ligand for the highly efficient, copper‐catalyzed asymmetric conjugate addition reaction of organozinc reagents with cycloalkenones, giving 3‐alkylated cycloalkanones in high enantioselectivity of up to 98 % ee . A model that predicts the stereochemistry of the reaction is discussed.