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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...

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Autores principales: Villaescusa, Leire, Hernández, Iker, Azcune, Laura, Rudi, Ainhoa, Mercero, José M., Landa, Aitor, Oiarbide, Mikel, Palomo, Claudio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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