Peptidic Amidomonophosphane Ligand for Copper‐Catalyzed Asymmetric Conjugate Addition of Diorganozincs to Cycloalkenones | Zendy

Soeta Takahiro | Zendy; Selim Khalid | Zendy; Kuriyama Masami | Zendy; Tomioka Kiyoshi | Zendy

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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

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.

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