Condensation of beta-hydroxy sulfones and vinyl sulfones with aldehydes and ketones using phenyllithium as base
Résumé
Condensation of beta-hydroxysulfones 7a-b with aldehydes and ketones were performed with diverse bases. Phenyllithium proved to be optimum, giving yields of compounds 9-12a-e ranging from 67 to 80%. Condensation of vinyl sulfones 15a-c with aldehydes also worked very well with PhLi, and the resulting adducts 16a-d were transformed into protected syn 1,3-diols flanked with an olefin at the a carbon by a new conjugate addition/elimination sequence. These products are models for the C21-C25 sub-unit of Dolabelides.
Domaines
Chimie organique
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