Chiral 2-acetamidoacrylates in conjugate addition – asymmetric enolate trapping reactions. Asymmetric synthesis of phenylalanine | Zendy

Carlos Cativiela | Zendy; María D. DíazdeVillegas | Zendy; José A. Gálvez | Zendy

Open Access

Chiral 2-acetamidoacrylates in conjugate addition – asymmetric enolate trapping reactions. Asymmetric synthesis of phenylalanine

Author(s) -

Carlos Cativiela,

María D. DíazdeVillegas,

José A. Gálvez

Publication year - 1992

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v92-294

Subject(s) - chemistry , protonation , diastereomer , enantioselective synthesis , conjugate , nucleophile , phenylalanine , reactivity (psychology) , phenylmagnesium bromide , stereochemistry , addition reaction , medicinal chemistry , bromide , chiral auxiliary , organic chemistry , amino acid , catalysis , medicine , ion , alternative medicine , pathology , reagent , mathematical analysis , biochemistry , mathematics

A new route to the asymmetric synthesis of α-amino acids based on the reactivity of chiral 2-acetamidoacrylates with nucleophiles through a conjugate addition followed by diastereoselective protonation of the enolate is described. Phenylalanine precursors are obtained in excellent chemical yields (80–95%) with moderate diastereomeric excess (0–44%) through the reaction of chiral 2-acetamidoacrylates with phenylmagnesium bromide in the presence of CuI followed by diastereoselective enolate protonation.

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