Realizing an Aza Paternò-Büchi Reaction.

Kumarasamy, Elango; Kandappa, Sunil Kumar; Raghunathan, Ramya; Jockusch, Steffen; Sivaguru, Jayaraman

Kumarasamy, Elango; Kandappa, Sunil Kumar; Raghunathan, Ramya; Jockusch, Steffen; Sivaguru, Jayaraman.

Afiliação

Kumarasamy E; Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58108, USA.
Kandappa SK; Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58108, USA.
Raghunathan R; Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58108, USA.
Jockusch S; Department of Chemistry, Columbia University, New York, NY, 10027, USA.
Sivaguru J; Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58108, USA.

Angew Chem Int Ed Engl ; 56(25): 7056-7061, 2017 06 12.

Article em En | MEDLINE | ID: mdl-28452104

ABSTRACT

ABSTRACT

Intramolecular atropselective aza Paternò-Büchi reaction involving atropisomeric enamide and imine functionalities under sensitized irradiation leads to azetidine products in good yield and selectivity (ee >96 %). A mechanistic model based on detailed photophysical and isomerization kinetic studies is provided that shed light into the reactivity of enamides leading to aza Paternò-Büchi reaction.

Palavras-chave

[2+2]-photocycloaddition; asymmetric photoreaction; atropselectivity; aza Paternò-Büchi reaction; imines

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2017 Tipo de documento: Article País de afiliação: Estados Unidos

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