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Enantioselective Addition of Remote Alkyl Radicals to Double Bonds by Photocatalytic Proton-Coupled Electron Transfer (PCET) Deconstruction of Unstrained Cycloalkanols

Author
Salaverri Mora, Noeliauntranslated; Carli, Benedetta; Díaz-Tendero Victoria, Sergiountranslated; Marzo Puerta, Leyreuntranslated; Alemán Lara, José Juliánuntranslated
Entity
UAM. Departamento de Química Orgánica
Publisher
American Chemical Society
Date
2022-04-01
Citation
Organic Letters 24.17 (2022): 3123–3127
ISSN
1523-7060 (print); 1523-7052 (online)
DOI
10.1021/acs.orglett.2c00662
Funded by
Financial support was provided by the Spanish Government (RTI2018-095038-B-I00, PID2019-110091GB-I00″), “Comunidad de Madrid” and European Structural Funds (S2018/ NMT-4367) and proyectos sinérgicos I+D (Y2020/NMT6469) and Comunidad Autónoma de Madrid (SI1/PJI/2019- 00237). N.S. thanks MINECO for an FPU predoctoral fellowship, and L.M. thanks CAM for an “Atracción de Talento Investigador” contract (2017-T2/AMB-5037). We acknowledge the generous allocation of computer time at the Centro de Computación Científica at the Universidad Autónoma de Madrid (CCC-UAM)
Project
Gobierno de España. RTI2018-095038-B-I00; Gobierno de España. PID2019-110091GB-I00; Comunidad de Madrid. SI1/PJI/2019- 00237
Editor's Version
https://doi.org/10.1021/acs.orglett.2c00662
Subjects
Química
URI
http://hdl.handle.net/10486/703089
Rights
© 2022 The Authors

Licencia Creative Commons
Esta obra está bajo una Licencia Creative Commons Atribución 4.0 Internacional.

Abstract

Herein, we report the enantioselective addition of remote alkyl radicals, generated from the ring opening of unstrained cycloalkanols by a proton-coupled electron transfer (PCET) process, to 2-acyl imidazoles previously coordinated to a rhodium-based chiral Lewis acid. High yields and enantioselectivites up to 99% are achieved in 1 h. Mechanistic investigations support the formation of the remote alkyl radical by a PCET process, and theoretical studies explain the observed stereochemistry in the addition step
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Google™ Scholar:Salaverri Mora, Noelia - Carli, Benedetta - Díaz-Tendero Victoria, Sergio - Marzo Puerta, Leyre - Alemán Lara, José Julián

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