Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter

[Image: see text] A highly enantioselective one-pot synthesis of functionalized triflones, bearing a quaternary stereocenter, has been developed, exploiting the Michael reaction of α-(trifluoromethylsulfonyl) aryl acetic acid esters with N-acryloyl-1H-pyrazole catalyzed by commercially available Tak...

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Autores principales: Franco, Francesca, Meninno, Sara, Overgaard, Jacob, Rossi, Sergio, Benaglia, Maurizio, Lattanzi, Alessandra
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490835/
https://www.ncbi.nlm.nih.gov/pubmed/35687515
http://dx.doi.org/10.1021/acs.orglett.2c01589
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author Franco, Francesca
Meninno, Sara
Overgaard, Jacob
Rossi, Sergio
Benaglia, Maurizio
Lattanzi, Alessandra
author_facet Franco, Francesca
Meninno, Sara
Overgaard, Jacob
Rossi, Sergio
Benaglia, Maurizio
Lattanzi, Alessandra
author_sort Franco, Francesca
collection PubMed
description [Image: see text] A highly enantioselective one-pot synthesis of functionalized triflones, bearing a quaternary stereocenter, has been developed, exploiting the Michael reaction of α-(trifluoromethylsulfonyl) aryl acetic acid esters with N-acryloyl-1H-pyrazole catalyzed by commercially available Takemoto’s catalyst, followed by nucleophilic acyl substitution with alcohols. Preliminary investigations highlighted the attractive potential of the triflinate anion as the leaving group for stereocontrolled postfunctionalizations.
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spelling pubmed-94908352022-09-22 Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter Franco, Francesca Meninno, Sara Overgaard, Jacob Rossi, Sergio Benaglia, Maurizio Lattanzi, Alessandra Org Lett [Image: see text] A highly enantioselective one-pot synthesis of functionalized triflones, bearing a quaternary stereocenter, has been developed, exploiting the Michael reaction of α-(trifluoromethylsulfonyl) aryl acetic acid esters with N-acryloyl-1H-pyrazole catalyzed by commercially available Takemoto’s catalyst, followed by nucleophilic acyl substitution with alcohols. Preliminary investigations highlighted the attractive potential of the triflinate anion as the leaving group for stereocontrolled postfunctionalizations. American Chemical Society 2022-06-10 2022-06-24 /pmc/articles/PMC9490835/ /pubmed/35687515 http://dx.doi.org/10.1021/acs.orglett.2c01589 Text en © 2022 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 Franco, Francesca
Meninno, Sara
Overgaard, Jacob
Rossi, Sergio
Benaglia, Maurizio
Lattanzi, Alessandra
Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter
title Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter
title_full Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter
title_fullStr Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter
title_full_unstemmed Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter
title_short Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter
title_sort catalytic enantioselective entry to triflones featuring a quaternary stereocenter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490835/
https://www.ncbi.nlm.nih.gov/pubmed/35687515
http://dx.doi.org/10.1021/acs.orglett.2c01589
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AT rossisergio catalyticenantioselectiveentrytotriflonesfeaturingaquaternarystereocenter
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