Rigidified Bis(sulfonyl)ethylenes as Effective Michael Acceptors for Asymmetric Catalysis: Application to the Enantioselective Synthesis of Quaternary Hydantoins
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...
| Autores: | , , , , , , , |
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| Tipo de documento: | artigo |
| Data de publicação: | 2023 |
| País: | España |
| Recursos: | Universidad del País Vasco |
| Repositório: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/66611 |
| Acesso em linha: | http://hdl.handle.net/10810/66611 |
| Access Level: | Acceso aberto |
| Palavra-chave: | Organocatalysis Hydantoins Quaternary stereocenters Bis(sulfonyl)ethylenes |
| Resumo: | 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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