NHC-Catalyzed Enantioselective Synthesis of Tetracyclic Î´-Lactones by (4 + 2) Annulation of <i>ortho</i>-Quinodimethanes with Activated Ketones.

Sarkar, Deeptanu; Barik, Shilpa; Shee, Sayan; Gonnade, Rajesh G; Biju, Akkattu T

NHC-Catalyzed Enantioselective Synthesis of Tetracyclic Î´-Lactones by (4 + 2) Annulation of ortho-Quinodimethanes with Activated Ketones.

Sarkar, Deeptanu; Barik, Shilpa; Shee, Sayan; Gonnade, Rajesh G; Biju, Akkattu T.

Afiliación

Sarkar D; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Barik S; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Shee S; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Gonnade RG; Centre for Materials Characterization, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India.
Biju AT; Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.

Org Lett ; 25(43): 7852-7857, 2023 Nov 03.

Article en En | MEDLINE | ID: mdl-37862445

RESUMEN

The N-heterocyclic carbene (NHC)-catalyzed generation of ortho-quinodimethanes (o-QDMs) from 9H-fluorene-1-carbaldehydes followed by the interception with activated ketones resulting in the enantioselective synthesis of tetracyclic Î´-lactones is presented. High diastereoselectivity of products, remote C(sp3)-H functionalization, broad substrate scope, and mild reaction conditions are the notable features of the present (4 + 2) annulation.

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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: 2023 Tipo del documento: Article País de afiliación: India Pais de publicación: Estados Unidos

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