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A catalytic enantioselective stereodivergent aldol reaction

The aldol reaction is among the most powerful and strategically important carbon–carbon bond–forming transformations in organic chemistry. The importance of the aldol reaction in constructing chiral building blocks for complex small-molecule synthesis has spurred continuous efforts toward the develo...

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Autores principales: Rahman, Md. Ataur, Cellnik, Torsten, Ahuja, Brij Bhushan, Li, Liang, Healy, Alan R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Association for the Advancement of Science 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10017038/
https://www.ncbi.nlm.nih.gov/pubmed/36921040
http://dx.doi.org/10.1126/sciadv.adg8776
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author Rahman, Md. Ataur
Cellnik, Torsten
Ahuja, Brij Bhushan
Li, Liang
Healy, Alan R.
author_facet Rahman, Md. Ataur
Cellnik, Torsten
Ahuja, Brij Bhushan
Li, Liang
Healy, Alan R.
author_sort Rahman, Md. Ataur
collection PubMed
description The aldol reaction is among the most powerful and strategically important carbon–carbon bond–forming transformations in organic chemistry. The importance of the aldol reaction in constructing chiral building blocks for complex small-molecule synthesis has spurred continuous efforts toward the development of direct catalytic variants. The realization of a general catalytic aldol reaction with control over both the relative and absolute configurations of the newly formed stereogenic centers has been a longstanding goal in the field. Here, we report a decarboxylative aldol reaction that provides access to all four possible stereoisomers of the aldol product in one step from identical reactants. The mild reaction can be carried out on a large scale in an open flask, and generates CO(2) as the only by-product. The method tolerates a broad substrate scope and generates chiral β-hydroxy thioester products with substantial downstream utility.
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spelling pubmed-100170382023-03-16 A catalytic enantioselective stereodivergent aldol reaction Rahman, Md. Ataur Cellnik, Torsten Ahuja, Brij Bhushan Li, Liang Healy, Alan R. Sci Adv Physical and Materials Sciences The aldol reaction is among the most powerful and strategically important carbon–carbon bond–forming transformations in organic chemistry. The importance of the aldol reaction in constructing chiral building blocks for complex small-molecule synthesis has spurred continuous efforts toward the development of direct catalytic variants. The realization of a general catalytic aldol reaction with control over both the relative and absolute configurations of the newly formed stereogenic centers has been a longstanding goal in the field. Here, we report a decarboxylative aldol reaction that provides access to all four possible stereoisomers of the aldol product in one step from identical reactants. The mild reaction can be carried out on a large scale in an open flask, and generates CO(2) as the only by-product. The method tolerates a broad substrate scope and generates chiral β-hydroxy thioester products with substantial downstream utility. American Association for the Advancement of Science 2023-03-15 /pmc/articles/PMC10017038/ /pubmed/36921040 http://dx.doi.org/10.1126/sciadv.adg8776 Text en Copyright © 2023 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution License 4.0 (CC BY). https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution license (https://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Physical and Materials Sciences
Rahman, Md. Ataur
Cellnik, Torsten
Ahuja, Brij Bhushan
Li, Liang
Healy, Alan R.
A catalytic enantioselective stereodivergent aldol reaction
title A catalytic enantioselective stereodivergent aldol reaction
title_full A catalytic enantioselective stereodivergent aldol reaction
title_fullStr A catalytic enantioselective stereodivergent aldol reaction
title_full_unstemmed A catalytic enantioselective stereodivergent aldol reaction
title_short A catalytic enantioselective stereodivergent aldol reaction
title_sort catalytic enantioselective stereodivergent aldol reaction
topic Physical and Materials Sciences
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10017038/
https://www.ncbi.nlm.nih.gov/pubmed/36921040
http://dx.doi.org/10.1126/sciadv.adg8776
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