Metal-Free Visible Light-Mediated Photocatalysis: Controlling Intramolecular [2 + 2] Photocycloaddition of Enones through Axial Chirality.

Clay, Anthony; Vallavoju, Nandini; Krishnan, Retheesh; Ugrinov, Angel; Sivaguru, Jayaraman

Clay, Anthony; Vallavoju, Nandini; Krishnan, Retheesh; Ugrinov, Angel; Sivaguru, Jayaraman.

Afiliação

Clay A; Department of Chemistry and Biochemistry, North Dakota State University , Fargo, North Dakota 58108, United States.
Vallavoju N; Department of Chemistry and Biochemistry, North Dakota State University , Fargo, North Dakota 58108, United States.
Krishnan R; Department of Chemistry and Biochemistry, North Dakota State University , Fargo, North Dakota 58108, United States.
Ugrinov A; Department of Chemistry and Biochemistry, North Dakota State University , Fargo, North Dakota 58108, United States.
Sivaguru J; Department of Chemistry and Biochemistry, North Dakota State University , Fargo, North Dakota 58108, United States.

J Org Chem ; 81(16): 7191-200, 2016 08 19.

Article em En | MEDLINE | ID: mdl-27382920

ABSTRACT

ABSTRACT

Atropisomeric enone-imides and enone-amides featuring N-CAryl bond rotation were evaluated for intramolecular [2 + 2] photocycloaddition. Straight addition product was observed over cross-addition product with good control over reactivity. The atropselectivity was found to be dependent on the substituent on the aryl ring. Substitution-dependent atropselectivity was rationalized on the basis of a divergent mechanistic pathway.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2016 Tipo de documento: Article País de afiliação: Estados Unidos

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