ArticleJournal of the American Chemical Society2020
Reaction Mechanism, Origins of Enantioselectivity, and Reactivity Trends in Asymmetric Allylic Alkylation: A Comprehensive Quantum Mechanics Investigation of a C(sp
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 10 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
10 citing papers in PubMed.
- Unplugging Asymmetric Synthesis with a Wireless, Self-Pumping Electrochemical Reactor.Journal of the American Chemical Society · 2025Article
- Enantioselective Michael Spirocyclization of Palladium Enolates.ACS catalysis · 2025Article
- Origins of Enhanced Enantioselectivity in the Pd-Catalyzed Decarboxylative Allylic Alkylation ofCatalysts (Basel, Switzerland) · 2023Article
- Divergent Catalysis: Catalytic Asymmetric [4+2] Cycloaddition of Palladium Enolates.Journal of the American Chemical Society · 2023Article
- Palladium-CatalyzedACS catalysis · 2022Article
- Enantioselective Total Synthesis of (-)-Limaspermidine and (-)-Kopsinine by a Nitroaryl Transfer Cascade Strategy.Angewandte Chemie (International ed. in English) · 2022Article
- Proofreading experimentally assigned stereochemistry through Q2MM predictions in Pd-catalyzed allylic aminations.Nature communications · 2021Article
- Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.Chemical reviews · 2021Article
- The Transition Metal Catalyzed [π2s + π2s + σ2s + σ2s] Pericyclic Reaction: Woodward-Hoffmann Rules, Aromaticity, and Electron Flow.Journal of the American Chemical Society · 2020Article
- Mechanisms, Challenges, and Opportunities of Dual Ni/Photoredox-Catalyzed C(spWiley interdisciplinary reviews. Computational molecular scienceArticle
Corrections and comments
- Erratum issued
Authors and funding
3 authors.
Funding
Abstract
We utilize quantum mechanics to evaluate a variety of plausible mechanistic pathways for the entirety of the catalytic cycle for asymmetric decarboxylative allylic alkylation of allyl β-ketoesters. We present a mechanistic picture that unites all current experimental observations, including enantioinduction, reaction rate, catalyst resting state, enolate crossover experiments, water tolerance, and the effects of solvation on inner- and outer-sphere mechanisms. Experiments designed to evaluate the fidelity and predictive power of the computational models reveal the methods employed herein to be highly effective in elucidating the reactivity of the catalytic system. On the basis of these findings, we highlight a computational framework from which chemically accurate results are obtained and address the current limitations of the decarboxylative asymmetric allylic alkylation reaction.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.