Kinetic Resolution Approach to the Synthesis of C-N Axially Chiral <i>N</i>-Aryl Aminomaleimides via NHC-Catalyzed [3 + 3] Annulation.

Barik, Soumen; Das, Rohan Chandra; Balanna, Kuruva; Biju, Akkattu T

Kinetic Resolution Approach to the Synthesis of C-N Axially Chiral N-Aryl Aminomaleimides via NHC-Catalyzed [3 + 3] Annulation.

Barik, Soumen; Das, Rohan Chandra; Balanna, Kuruva; Biju, Akkattu T.

Afiliación

Barik S; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Das RC; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Balanna K; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Biju AT; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.

Org Lett ; 24(29): 5456-5461, 2022 Jul 29.

Article en En | MEDLINE | ID: mdl-35856856

RESUMEN

Chiral NHC-catalyzed kinetic resolution of N-aryl aminomaleimides allowing the synthesis of C-N axially chiral N-aryl aminomaleimides via remote chirality control is presented. The catalytically generated α,ß-unsaturated acylazoliums from 2-bromoenals underwent selective [3 + 3] annulation with one of the enantiomers of maleimide to furnish fused-dihydropyridinone (bearing axial/central chirality, up to 6:1 dr, >99:1 er) leaving the enantioenriched opposite enantiomer (up to >99:1 er). Studies on C-N bond rotation barrier and dependence on temperature are also provided.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article País de afiliación: India Pais de publicación: Estados Unidos

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