Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates.

Nair, Deepa; Tiwari, Abhishek; Laha, Banamali; Namboothiri, Irishi N N

Nair, Deepa; Tiwari, Abhishek; Laha, Banamali; Namboothiri, Irishi N N.

Afiliación

Nair D; Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.
Tiwari A; Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.
Laha B; Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.
Namboothiri INN; Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.

Beilstein J Org Chem ; 20: 2016-2023, 2024.

Article en En | MEDLINE | ID: mdl-39161707

ABSTRACT

ABSTRACT

A cascade inter-intramolecular double Michael strategy for the synthesis of highly functionalized cyclohexanones from curcumins and arylidenemalonates is reported. This strategy works in the presence of aqueous KOH using TBAB as a suitable phase transfer catalyst at room temperature. The functionalized cyclohexanones are formed as major products in moderate to excellent yields with complete diastereoselectivity in most cases. A triple Michael adduct, tetrahydrochromen-4-one, is also formed as a side product in a few cases with excellent diastereoselectivity.

Palabras clave

Michael reaction; arylidenemalonates; curcumins; cyclohexanones; diastereoselective synthesis; tetrahydrochromenones

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Beilstein J Org Chem Año: 2024 Tipo del documento: Article País de afiliación: India Pais de publicación: Alemania

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