Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism

[Image: see text] A novel methodology for the epoxidation of a broad range of primary, secondary, and tertiary allylic alcohols is described using tert-butyl hydroperoxide as oxidant and Ti(III) species generated by reduction of Ti(IV) complexes, with manganese (0) in 1,4-dioxane under mild reaction...

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Autores principales: Botubol-Ares, José Manuel, Hanson, James R., Hernández-Galán, Rosario, Collado, Isidro G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641598/
https://www.ncbi.nlm.nih.gov/pubmed/31457640
http://dx.doi.org/10.1021/acsomega.7b00386
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author Botubol-Ares, José Manuel
Hanson, James R.
Hernández-Galán, Rosario
Collado, Isidro G.
author_facet Botubol-Ares, José Manuel
Hanson, James R.
Hernández-Galán, Rosario
Collado, Isidro G.
author_sort Botubol-Ares, José Manuel
collection PubMed
description [Image: see text] A novel methodology for the epoxidation of a broad range of primary, secondary, and tertiary allylic alcohols is described using tert-butyl hydroperoxide as oxidant and Ti(III) species generated by reduction of Ti(IV) complexes, with manganese (0) in 1,4-dioxane under mild reaction conditions. The reaction proceeded with wide substrate scope and high chemo- and diastereoselectivity. A mechanistic pathway for the reaction is also discussed.
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spelling pubmed-66415982019-08-27 Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism Botubol-Ares, José Manuel Hanson, James R. Hernández-Galán, Rosario Collado, Isidro G. ACS Omega [Image: see text] A novel methodology for the epoxidation of a broad range of primary, secondary, and tertiary allylic alcohols is described using tert-butyl hydroperoxide as oxidant and Ti(III) species generated by reduction of Ti(IV) complexes, with manganese (0) in 1,4-dioxane under mild reaction conditions. The reaction proceeded with wide substrate scope and high chemo- and diastereoselectivity. A mechanistic pathway for the reaction is also discussed. American Chemical Society 2017-07-03 /pmc/articles/PMC6641598/ /pubmed/31457640 http://dx.doi.org/10.1021/acsomega.7b00386 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Botubol-Ares, José Manuel
Hanson, James R.
Hernández-Galán, Rosario
Collado, Isidro G.
Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism
title Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism
title_full Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism
title_fullStr Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism
title_full_unstemmed Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism
title_short Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism
title_sort mild epoxidation of allylic alcohols catalyzed by titanium(iii) complexes: selectivity and mechanism
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641598/
https://www.ncbi.nlm.nih.gov/pubmed/31457640
http://dx.doi.org/10.1021/acsomega.7b00386
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