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Highly Enantioselective Catalytic Lactonization at Nonactivated Primary and Secondary γ-C–H Bonds
[Image: see text] Chiral oxygenated aliphatic moieties are recurrent in biological and pharmaceutically relevant molecules and constitute one of the most versatile types of functionalities for further elaboration. Herein we report a protocol for straightforward and general access to chiral γ-lactone...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10507665/ https://www.ncbi.nlm.nih.gov/pubmed/37540636 http://dx.doi.org/10.1021/jacs.3c06231 |
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author | Call, Arnau Capocasa, Giorgio Palone, Andrea Vicens, Laia Aparicio, Eric Choukairi Afailal, Najoua Siakavaras, Nikos López Saló, Maria Eugènia Bietti, Massimo Costas, Miquel |
author_facet | Call, Arnau Capocasa, Giorgio Palone, Andrea Vicens, Laia Aparicio, Eric Choukairi Afailal, Najoua Siakavaras, Nikos López Saló, Maria Eugènia Bietti, Massimo Costas, Miquel |
author_sort | Call, Arnau |
collection | PubMed |
description | [Image: see text] Chiral oxygenated aliphatic moieties are recurrent in biological and pharmaceutically relevant molecules and constitute one of the most versatile types of functionalities for further elaboration. Herein we report a protocol for straightforward and general access to chiral γ-lactones via enantioselective oxidation of strong nonactivated primary and secondary C(sp(3))–H bonds in readily available carboxylic acids. The key enabling aspect is the use of robust sterically encumbered manganese catalysts that provide outstanding enantioselectivities (up to >99.9%) and yields (up to 96%) employing hydrogen peroxide as the oxidant. The resulting γ-lactones are of immediate interest for the preparation of inter alia natural products and recyclable polymeric materials. |
format | Online Article Text |
id | pubmed-10507665 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-105076652023-09-20 Highly Enantioselective Catalytic Lactonization at Nonactivated Primary and Secondary γ-C–H Bonds Call, Arnau Capocasa, Giorgio Palone, Andrea Vicens, Laia Aparicio, Eric Choukairi Afailal, Najoua Siakavaras, Nikos López Saló, Maria Eugènia Bietti, Massimo Costas, Miquel J Am Chem Soc [Image: see text] Chiral oxygenated aliphatic moieties are recurrent in biological and pharmaceutically relevant molecules and constitute one of the most versatile types of functionalities for further elaboration. Herein we report a protocol for straightforward and general access to chiral γ-lactones via enantioselective oxidation of strong nonactivated primary and secondary C(sp(3))–H bonds in readily available carboxylic acids. The key enabling aspect is the use of robust sterically encumbered manganese catalysts that provide outstanding enantioselectivities (up to >99.9%) and yields (up to 96%) employing hydrogen peroxide as the oxidant. The resulting γ-lactones are of immediate interest for the preparation of inter alia natural products and recyclable polymeric materials. American Chemical Society 2023-08-04 /pmc/articles/PMC10507665/ /pubmed/37540636 http://dx.doi.org/10.1021/jacs.3c06231 Text en © 2023 American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Call, Arnau Capocasa, Giorgio Palone, Andrea Vicens, Laia Aparicio, Eric Choukairi Afailal, Najoua Siakavaras, Nikos López Saló, Maria Eugènia Bietti, Massimo Costas, Miquel Highly Enantioselective Catalytic Lactonization at Nonactivated Primary and Secondary γ-C–H Bonds |
title | Highly Enantioselective
Catalytic Lactonization at
Nonactivated Primary and Secondary γ-C–H
Bonds |
title_full | Highly Enantioselective
Catalytic Lactonization at
Nonactivated Primary and Secondary γ-C–H
Bonds |
title_fullStr | Highly Enantioselective
Catalytic Lactonization at
Nonactivated Primary and Secondary γ-C–H
Bonds |
title_full_unstemmed | Highly Enantioselective
Catalytic Lactonization at
Nonactivated Primary and Secondary γ-C–H
Bonds |
title_short | Highly Enantioselective
Catalytic Lactonization at
Nonactivated Primary and Secondary γ-C–H
Bonds |
title_sort | highly enantioselective
catalytic lactonization at
nonactivated primary and secondary γ-c–h
bonds |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10507665/ https://www.ncbi.nlm.nih.gov/pubmed/37540636 http://dx.doi.org/10.1021/jacs.3c06231 |
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