Work

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

Year: 2024

Type: article

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.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.20.177

Authors: Deepa Nair, Abhishek Tiwari, Banamali Laha, Irishi N N Namboothiri

Institution: Indian Institute of Technology Bombay

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Ministry of Education, India, Indian Institute of Technology Bombay, Science and Engineering Research Board

Award: G2970259236