Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis

[Image: see text] We have developed a new three-component catalytic coupling reaction of alkynyl boronates, diazomethanes, and aliphatic/aromatic ketones in the presence of BINOL derivatives. The reaction proceeds with a remarkably high enantio- and diastereoselectivity (up to three contiguous stere...

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Autores principales: Deliaval, Marie, Jayarajan, Ramasamy, Eriksson, Lars, Szabó, Kálmán J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10176480/
https://www.ncbi.nlm.nih.gov/pubmed/37126044
http://dx.doi.org/10.1021/jacs.3c02852
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author Deliaval, Marie
Jayarajan, Ramasamy
Eriksson, Lars
Szabó, Kálmán J.
author_facet Deliaval, Marie
Jayarajan, Ramasamy
Eriksson, Lars
Szabó, Kálmán J.
author_sort Deliaval, Marie
collection PubMed
description [Image: see text] We have developed a new three-component catalytic coupling reaction of alkynyl boronates, diazomethanes, and aliphatic/aromatic ketones in the presence of BINOL derivatives. The reaction proceeds with a remarkably high enantio- and diastereoselectivity (up to three contiguous stereocenters) affording tertiary CF(3)-allenols in a single operational step. The reaction proceeds under mild, neutral, metal-free conditions, which leads to a high level of functional group tolerance.
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spelling pubmed-101764802023-05-13 Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis Deliaval, Marie Jayarajan, Ramasamy Eriksson, Lars Szabó, Kálmán J. J Am Chem Soc [Image: see text] We have developed a new three-component catalytic coupling reaction of alkynyl boronates, diazomethanes, and aliphatic/aromatic ketones in the presence of BINOL derivatives. The reaction proceeds with a remarkably high enantio- and diastereoselectivity (up to three contiguous stereocenters) affording tertiary CF(3)-allenols in a single operational step. The reaction proceeds under mild, neutral, metal-free conditions, which leads to a high level of functional group tolerance. American Chemical Society 2023-04-26 /pmc/articles/PMC10176480/ /pubmed/37126044 http://dx.doi.org/10.1021/jacs.3c02852 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Deliaval, Marie
Jayarajan, Ramasamy
Eriksson, Lars
Szabó, Kálmán J.
Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis
title Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis
title_full Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis
title_fullStr Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis
title_full_unstemmed Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis
title_short Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis
title_sort three-component approach to densely functionalized trifluoromethyl allenols by asymmetric organocatalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10176480/
https://www.ncbi.nlm.nih.gov/pubmed/37126044
http://dx.doi.org/10.1021/jacs.3c02852
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