The Effect of High Pressure on the Diastereoselectivity of Intermolecular All-Carbon Diels–Alder Reactions

Tietze, Lutz F.; Henrich, Marielouise; Niklaus, Anja; Buback, Michael

doi:10.1002/(sici)1521-3765(19990104)5:1<297::aid-chem297>3.3.co;2-x

Chem. Eur. J.

1999

DOI: 10.1002/(sici)1521-3765(19990104)5:1<297::aid-chem297>3.3.co;2-x

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The Effect of High Pressure on the Diastereoselectivity of Intermolecular All-Carbon Diels–Alder Reactions

Lutz F. Tietze

Marielouise Henrich

Anja Niklaus

et al.

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2020

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“…Generally, the more compact endo approach is favored by a HPs. 2,19,20 In some cases endo kinetic adducts are obtained under hyperbaric cycloaddition, while exo thermodynamic ones are generated by heating. 21 The activation observed in organic reactions in liquid phase is explained by the Evans-Polanyi equation, which connects a negative activation volume with the acceleration of the reaction with pressure increase.…”

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confidence: 99%

Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions

Loco¹,

Spezia²,

Cartier³

et al. 2020

Preprint

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High pressure effects on the Diels-Alder reaction in condensed phase are investigated by means oftheoretical methods, employing advanced multiscale modeling approaches based on physically groundedmodels. The simulations reveal how the increase of pressure from 1 to 10000 atm does not affect thestability of the reaction products, modifying the kinetics of the process by lowering considerably thetransition state energy. The reaction profile at high pressure remarkably differs from that at 1 atm,showing a submerged TS and a pre–TS structure lower in energy. The different solvation between endoand exo pre–TS is revealed as the driving force pushing the reaction toward a much higher preferencefor the endo product at high pressure.

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mentioning

confidence: 99%

Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions

Loco¹,

Spezia²,

Cartier³

et al. 2020

Preprint

View full text Add to dashboard Cite

show abstract

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The Effect of High Pressure on the Diastereoselectivity of Intermolecular All-Carbon Diels–Alder Reactions

Cited by 1 publication

References 0 publications

Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions

Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions

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