Diastereoselective, Lewis acid-mediated Diels–Alder reactions of allenoic acid derivatives and 1,3-cyclopentadienes

Harvey, Freya M.; Heidecker, Alexandra A.; Merten, Christian; Bach, Thorsten

doi:10.1039/d3ob00598d

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00598d

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Diastereoselective, Lewis acid-mediated Diels–Alder reactions of allenoic acid derivatives and 1,3-cyclopentadienes

Freya M. Harvey

Alexandra A. Heidecker

Christian Merten

et al.

Abstract: Allenes with different substituents at their terminal carbon atom display axial chirality and can be obtained in enantiopure form by a photochemical deracemization protocol. It has now been studied under...

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MEDT analysis of mechanism and selectivities in non-catalyzed and lewis acid-catalyzed diels–alder reactions between R-carvone and isoprene

Idrissi,

Abdoul-Hakim,

Saleh

et al. 2024

Sci Rep

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Within the context of Molecular Electronic Density Theory (MEDT), this study investigates the Diels–Alder reaction among isoprene (2) and R-carvone (1R) applying DFT simulations, with and without Lewis acid (LA) catalysis. The results show that carvone (1R) acts as an electrophile and isoprene (2) as a nucleophile in a polar process. LA catalysis increases the electrophilicity of carvone, thereby improving the reactivity and selectivity of the reaction by reducing the activation Gibbs free energy. Parr functions reveal that the C5=C6 double bond is more reactive than the C9=C10 double bond, indicating chemoselectivity. The examination of the Electron Localization Function (ELF) reveals high regio- and stereoselectivity, indicating an asynchronous mechanism for the LA-catalyzed DA reaction. Furthermore, it is suggested that cycloadduct 3 has great anti-HIV potential because it exhibits lower binding energies than azidothymidine (AZT) in the docking studies of cycloadducts 3 and 4 amongst a primary HIV-1protein (1A8O plus 5W4Q).

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MEDT analysis of mechanism and selectivities in non-catalyzed and lewis acid-catalyzed diels–alder reactions between R-carvone and isoprene

Idrissi,

Abdoul-Hakim,

Saleh

et al. 2024

Sci Rep

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

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Diastereoselective, Lewis acid-mediated Diels–Alder reactions of allenoic acid derivatives and 1,3-cyclopentadienes

Abstract: Allenes with different substituents at their terminal carbon atom display axial chirality and can be obtained in enantiopure form by a photochemical deracemization protocol. It has now been studied under...

Cited by 1 publication

References 84 publications

MEDT analysis of mechanism and selectivities in non-catalyzed and lewis acid-catalyzed diels–alder reactions between R-carvone and isoprene

MEDT analysis of mechanism and selectivities in non-catalyzed and lewis acid-catalyzed diels–alder reactions between R-carvone and isoprene

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