Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates DOI Creative Commons
Deepa Nair, Abhishek Tiwari, Banamali Laha

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2016 - 2023

Published: Aug. 15, 2024

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

Language: Английский

The Michael donor–acceptor reactivity of curcumins in the synthesis of diverse multi-functional scaffolds DOI
Banamali Laha,

Abhishek R. Tiwari,

Edmond Gravel

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(7), P. 1346 - 1359

Published: Jan. 1, 2024

Curcumin and its analogs, display Michael donor–acceptor ability with various reactants in the presence of bases, Lewis acids catalysts, under conventional, microwave mechanochemical conditions generate diverse synthetic scaffolds.

Language: Английский

Citations

4
Cu(II) salen complex grafted onto KCC-1 as a convenient multifunctional heterogeneous catalyst for the preparation of 4H-benzochromenes DOI

Khadije Ghabdian,

Alireza Motavalizadehkakhky, Rahele Zhiani

et al.

Research on Chemical Intermediates, Journal Year: 2024, Volume and Issue: 50(7), P. 3179 - 3196

Published: May 20, 2024

Language: Английский

Citations

1
Enantioselective Desymmetrization of Curcumins with 3‐Olefinic Oxindoles for the Synthesis of Spirocyclohexanoneoxindoles DOI
Chenikkayala Siva Sankara, Shweta Bhagat, Ajeet Chandra

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(15)

Published: Feb. 24, 2023

Abstract An enantioselective desymmetrization of curcumins with 3‐olefinic oxindoles involving a cascade double‐Michael addition strategy provides direct access to spirocyclohexanone‐oxindoles complete regio‐ and diastereoselectivities excellent enantioselectivities, besides good yields. The products possess three contiguous chiral centers multiple reactive functionalities. observed selectivities were rationalized by transitions state energy calculations at B3LYP//6‐31g(d) level DFT.

Language: Английский

Citations

3
Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates DOI Creative Commons
Deepa Nair, Abhishek Tiwari, Banamali Laha

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2016 - 2023

Published: Aug. 15, 2024

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

Language: Английский

Citations

0