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Rigidified Bis(sulfonyl)ethylenes as Effective Michael Acceptors for Asymmetric Catalysis: Application to the Enantioselective Synthesis of Quaternary Hydantoins
[Image: see text] The catalytic, enantio- and diastereoselective addition of hydantoin surrogates II to “rigidified” vinylidene bis(sulfone) reagents is developed, thus overcoming the inability of commonly employed β-substituted vinylic sulfones to react. Adducts are transformed in enantioenriched 5...
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/PMC10013931/ https://www.ncbi.nlm.nih.gov/pubmed/36630318 http://dx.doi.org/10.1021/acs.joc.2c02403 |
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author | Villaescusa, Leire Hernández, Iker Azcune, Laura Rudi, Ainhoa Mercero, José M. Landa, Aitor Oiarbide, Mikel Palomo, Claudio |
author_facet | Villaescusa, Leire Hernández, Iker Azcune, Laura Rudi, Ainhoa Mercero, José M. Landa, Aitor Oiarbide, Mikel Palomo, Claudio |
author_sort | Villaescusa, Leire |
collection | PubMed |
description | [Image: see text] The catalytic, enantio- and diastereoselective addition of hydantoin surrogates II to “rigidified” vinylidene bis(sulfone) reagents is developed, thus overcoming the inability of commonly employed β-substituted vinylic sulfones to react. Adducts are transformed in enantioenriched 5,5-disubstituted hydantoins through hydrolysis and reductive desulfonylation processes providing new structures for eventual bioassays. Density functional theory studies that rationalize the observed reactivity and stereoselectivity trends are also provided. |
format | Online Article Text |
id | pubmed-10013931 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-100139312023-03-15 Rigidified Bis(sulfonyl)ethylenes as Effective Michael Acceptors for Asymmetric Catalysis: Application to the Enantioselective Synthesis of Quaternary Hydantoins Villaescusa, Leire Hernández, Iker Azcune, Laura Rudi, Ainhoa Mercero, José M. Landa, Aitor Oiarbide, Mikel Palomo, Claudio J Org Chem [Image: see text] The catalytic, enantio- and diastereoselective addition of hydantoin surrogates II to “rigidified” vinylidene bis(sulfone) reagents is developed, thus overcoming the inability of commonly employed β-substituted vinylic sulfones to react. Adducts are transformed in enantioenriched 5,5-disubstituted hydantoins through hydrolysis and reductive desulfonylation processes providing new structures for eventual bioassays. Density functional theory studies that rationalize the observed reactivity and stereoselectivity trends are also provided. American Chemical Society 2023-01-11 /pmc/articles/PMC10013931/ /pubmed/36630318 http://dx.doi.org/10.1021/acs.joc.2c02403 Text en © 2023 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 | Villaescusa, Leire Hernández, Iker Azcune, Laura Rudi, Ainhoa Mercero, José M. Landa, Aitor Oiarbide, Mikel Palomo, Claudio Rigidified Bis(sulfonyl)ethylenes as Effective Michael Acceptors for Asymmetric Catalysis: Application to the Enantioselective Synthesis of Quaternary Hydantoins |
title | Rigidified Bis(sulfonyl)ethylenes
as Effective Michael
Acceptors for Asymmetric Catalysis: Application to the Enantioselective
Synthesis of Quaternary Hydantoins |
title_full | Rigidified Bis(sulfonyl)ethylenes
as Effective Michael
Acceptors for Asymmetric Catalysis: Application to the Enantioselective
Synthesis of Quaternary Hydantoins |
title_fullStr | Rigidified Bis(sulfonyl)ethylenes
as Effective Michael
Acceptors for Asymmetric Catalysis: Application to the Enantioselective
Synthesis of Quaternary Hydantoins |
title_full_unstemmed | Rigidified Bis(sulfonyl)ethylenes
as Effective Michael
Acceptors for Asymmetric Catalysis: Application to the Enantioselective
Synthesis of Quaternary Hydantoins |
title_short | Rigidified Bis(sulfonyl)ethylenes
as Effective Michael
Acceptors for Asymmetric Catalysis: Application to the Enantioselective
Synthesis of Quaternary Hydantoins |
title_sort | rigidified bis(sulfonyl)ethylenes
as effective michael
acceptors for asymmetric catalysis: application to the enantioselective
synthesis of quaternary hydantoins |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10013931/ https://www.ncbi.nlm.nih.gov/pubmed/36630318 http://dx.doi.org/10.1021/acs.joc.2c02403 |
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