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2-Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis.

ABSTRACT: An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of ?,?-diamino acid derivatives with excellent stereoselectivity.

SUBMITTER: Guerrero-Corella A

PROVIDER: S-EPMC5947601 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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2-Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis.

Guerrero-Corella Andrea A Esteban Francisco F Iniesta Manuel M Martín-Somer Ana A Martín-Somer Ana A Parra Mario M Díaz-Tendero Sergio S Fraile Alberto A Alemán Jose J

Angewandte Chemie (International ed. in English) 20180414 19

An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ-diamino acid derivatives with excellent stereoselectivity. ...[more]

PMID: 29493860

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