Diastereoselective Synthesis of Highly Substituted Cyclohexanones and Tetrahydrochromene-4-ones Via Conjugate Addition of Curcumins to Arylidenemalonates

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2024 Aug 20

PMID 39161707

Authors

Deepa Nair

Abhishek Tiwari

Banamali Laha

Irishi N N Namboothiri

Affiliations

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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.

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