Retro-Cope elimination of cyclic alkynes: reactivity trends and rational design of next-generation bioorthogonal reagents

Beutick, Steven E.; Yu, Song; Orian, Laura; Bickelhaupt, F. Matthias; Hamlin, Trevor A.

doi:10.1039/d4sc04211e

Chem. Sci.

2024

DOI: 10.1039/d4sc04211e

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Retro-Cope elimination of cyclic alkynes: reactivity trends and rational design of next-generation bioorthogonal reagents

Steven E. Beutick,

Song Yu,

Laura Orian

et al.

Abstract: Diversify your bonds! The reactivity of preactivated cycloalkynes in the retro-Cope elimination reaction was quantum chemically investigated. Based on our finding, we rationally designed a suite of next-generation reagents.

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Understanding the Reactivity and Selectivity of Oxazaborolidium Ion‐Catalyzed Diels‐Alder Reactions Involving Cyclobutenones as Dienophiles

Portela,

Fernández

2024

ChemPlusChem

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The poorly understood factors controlling the reactivity and selectivity (both stereo‐ and enantioselectivity) of catalyzed Diels‐Alder reactions involving cyclobutenones as dienophiles have been analyzed in detail by means of Density Functional Theory calculations. To this end, the reactions with cyclopentadiene and furan as dienes and 3‐(methoxycarbonyl)cyclobutenone catalyzed by Corey’s chiral oxazaborolidium ion (COBI) have been selected and compared to their analogous uncatalyzed transformation. The combined Activation Strain Model of reactivity and Energy Decomposition Analysis methods have been used to quantitatively understand the acceleration and selectivity induced by the catalyst in this transformation.

show abstract

Understanding the Reactivity and Selectivity of Oxazaborolidium Ion‐Catalyzed Diels‐Alder Reactions Involving Cyclobutenones as Dienophiles

Portela,

Fernández

2024

ChemPlusChem

View full text Add to dashboard Cite

show abstract

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Retro-Cope elimination of cyclic alkynes: reactivity trends and rational design of next-generation bioorthogonal reagents

Abstract: Diversify your bonds! The reactivity of preactivated cycloalkynes in the retro-Cope elimination reaction was quantum chemically investigated. Based on our finding, we rationally designed a suite of next-generation reagents.

Cited by 1 publication

References 75 publications

Understanding the Reactivity and Selectivity of Oxazaborolidium Ion‐Catalyzed Diels‐Alder Reactions Involving Cyclobutenones as Dienophiles

Understanding the Reactivity and Selectivity of Oxazaborolidium Ion‐Catalyzed Diels‐Alder Reactions Involving Cyclobutenones as Dienophiles

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