The activation strain model of chemical reactivity

WJ van Zeist, FM Bickelhaupt - Organic & biomolecular chemistry, 2010 - pubs.rsc.org
Herein, we provide an account of the activation strain model of chemical reactivity and its
recent applications. In this model, the potential energy surface ΔE (ζ) along the reaction …

The role of aryne distortions, steric effects, and charges in regioselectivities of aryne reactions

JM Medina, JL Mackey, NK Garg… - Journal of the American …, 2014 - ACS Publications
The distortion/interaction model has been used to explain and predict reactivity in a variety
of reactions where more common explanations, such as steric and electronic factors, do not …

Diversity-oriented approaches to polycyclics and bioinspired molecules via the Diels–Alder strategy: Green chemistry, synthetic economy, and beyond

S Kotha, AS Chavan, D Goyal - ACS Combinatorial Science, 2015 - ACS Publications
We describe diverse approaches to various dienes and their utilization in the Diels–Alder
reaction to produce a variety of polycycles. The dienes covered here are prepared by simple …

Enantioselective organocatalytic diels-alder reactions

P Merino, E Marqués-López, T Tejero, RP Herrera - Synthesis, 2010 - thieme-connect.com
Abstract Enantioselective organocatalytic asymmetric Diels-Alder reactions provide a facile
and efficient route to optically active functionalized cyclohexenes, which can be further …

Alternative Mechanistic Explanation for Ligand-Dependent Selectivities in Copper-Catalyzed N- and O-Arylation Reactions

HZ Yu, YY Jiang, Y Fu, L Liu - Journal of the American Chemical …, 2010 - ACS Publications
The ligand-dependent selectivities in Ullmann-type reactions of amino alcohols with
iodobenzene by β-diketone-and 1, 10-phenanthroline-ligated CuI complexes were recently …

Diastereodivergent cis-and trans-fused [4+ 2] annulations of cyclic 1, 3-dienes and 1-azadienes via ligand-controlled palladium catalysis

Y Hu, JY Huang, RJ Yan, ZC Chen, Q Ouyang… - Chemical …, 2023 - pubs.rsc.org
Despite the blossoming of reports of diastereodivergent synthesis over the past years,
switchable control of the stereochemistry of the bridgehead atoms of the fused frameworks …

Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes

SM Bronner, JL Mackey, KN Houk… - Journal of the American …, 2012 - ACS Publications
We report an experimental and computational study of 3-silylarynes. The addition of
nucleophiles yield ortho-substituted products as a result of aryne distortion, but meta …

Catalytic carbonyl-olefin metathesis of aliphatic ketones: Iron (III) homo-dimers as lewis acidic superelectrophiles

H Albright, PS Riehl, CC McAtee, JP Reid… - Journal of the …, 2018 - ACS Publications
Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful
tool for carbon–carbon bond formation. However, currently available synthetic protocols rely …

Experimental Diels–Alder Reactivities of Cycloalkenones and Cyclic Dienes Explained through Transition‐State Distortion Energies

RS Paton, S Kim, AG Ross, SJ Danishefsky… - Angewandte …, 2011 - Wiley Online Library
The power of the Diels–Alder reaction was expanded recently through the discovery by Li
and Danishefsky that cyclobutenone is an unusually reactive dienophile; importantly, the …

Synthesis of pleuromutilin

NJ Foy, SV Pronin - Journal of the American Chemical Society, 2022 - ACS Publications
Synthesis of a potent inhibitor of bacterial protein synthesis, pleuromutilin, is described.
Assembly of the critical cyclooctane fragment relies on an oxidative ring-expansion, and …