Certain organic reaction pathways proceed via ambimodal transition states
Multiple computational and mechanistic studies confirm that certain organic reaction pathways proceed via ambimodal transition states, which undergo post-transition state bifurcation to yield multiple distinct products.
The retrieved papers provide extensive theoretical and computational evidence (via DFT calculations and molecular dynamics simulations) detailing organic reactions that proceed through ambimodal transition states and post-transition state bifurcations. The claim is fully supported.
Zhang H, Novak AJE, Jamieson CS, Xue XS, Chen S, Trauner D, Houk KN. Computational Exploration of the Mechanism of Critical Steps in the Biomimetic Synthesis of Preuisolactone A, and Discovery of New Ambimodal (5 + 2)/(4 + 2) Cycloadditions.. 2021. https://doi.org/10.1021/jacs.1c01856
Paper [0] identifies an ambimodal transition state leading to both (5 + 2) and (4 + 2) cycloaddition products.
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Zou Y, Houk KN. Mechanisms and Dynamics of Synthetic and Biosynthetic Formation of Delitschiapyrones: Solvent Control of Ambimodal Periselectivity.. 2021. https://doi.org/10.1021/jacs.1c05293
Paper [1] demonstrates variable selectivity originating from a (4 + 2)/(4 + 3) ambimodal transition state.
Martin-Somer A, Xue XS, Jamieson CS, Zou Y, Houk KN. Computational Design of a Tetrapericyclic Cycloaddition and the Nature of Potential Energy Surfaces with Multiple Bifurcations.. 2023. https://doi.org/10.1021/jacs.2c12871
Paper [4] explores an ambimodal transition state leading to four different pericyclic reaction products.
Hou Y, Chen J, Liu W, Zhu G, Yang Q, Wang X. Using the Theozyme Model to Study the Dynamical Mechanism of the Post-Transition State Bifurcation Reaction by NgnD Enzyme.. 2024. https://doi.org/10.3390/molecules29235518
Paper [8] investigates post-transition state bifurcation where a single ambimodal transition state yields multiple adducts.
Zhang Y, Cao C, She Y, Davies HML, Yang YF, Houk KN. Molecular Dynamics of the Davies Ambimodal C-H Functionalization/Cope Rearrangement Reaction.. 2024. https://doi.org/10.1021/acs.joc.4c01682
Paper [9] reports quasi-classical trajectories for a reaction proceeding via an ambimodal transition state toward multiple products.
Shin W, Hou Y, Wang X, Yang ZJ. Interplay between Energy and Entropy Mediates Ambimodal Selectivity of Cycloadditions.. 2024. https://doi.org/10.1021/acs.jctc.4c01138
Paper [11] analyzes how energy and entropy mediate the ambimodal selectivity of cycloadditions sharing a single transition state.
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