A general route to mono- and disubstituted divinyl sulfones: acyclic Michael acceptors for the synthesis of polyfunctionalized cyclic sulfones.
J Org Chem
; 76(9): 3034-41, 2011 May 06.
Article
em En
| MEDLINE
| ID: mdl-21438598
ABSTRACT
Nucleophilic C-S bond formation using easily available ß-hydroxysulfonate derivatives allowed direct access to new mono- and disubstituted divinyl sulfones. Our strategy uses thioethanol (HSCH(2)CH(2)OH) and its analogues such as HSCH(2)CH(Y)OH generated in situ. The strategy also allows the synthesis of modified divinyl sulfones attached to chiral appendages like carbohydrates. Bis-heteronucleophilic Michael addition reactions with 1 equiv of a primary amine afforded new generations of S,S-dioxothiomorpholine derivatives known for their therapeutic applications. Further synthetic manipulations of some of these cyclic compounds led to the synthesis of novel bicyclic derivatives.
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1
Base de dados:
MEDLINE
Assunto principal:
Sulfonas
/
Compostos Bicíclicos Heterocíclicos com Pontes
Idioma:
En
Ano de publicação:
2011
Tipo de documento:
Article