A conjugate addition/sulfoxide elimination route to allylic difluorophosphonates

Cerium-mediated conjugate additions of (diethoxyphosphinoyl) difluoromethyllithium to cyclic vinyl sulfoxides proceeded smoothly; thermal sulfoxide elimination afforded the products of formal vinylation, attaching the difluoromethylenephosphonato group to an alkenyl carbon atom. With acyclic vinyl s...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 49; pp. 9085 - 9088
Main Authors Blades, Kevin, Percy, Jonathan M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.12.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SULFONES
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Summary:Cerium-mediated conjugate additions of (diethoxyphosphinoyl) difluoromethyllithium to cyclic vinyl sulfoxides proceeded smoothly; thermal sulfoxide elimination afforded the products of formal vinylation, attaching the difluoromethylenephosphonato group to an alkenyl carbon atom. With acyclic vinyl sulfoxides, the addition occurred in moderate to poor yield. Addition failed completely in the absence of cerium(III) chloride, and was facilitated by an excess of the reagent. Cerium-mediated conjugate additions of [(diethoxyphosphinyl)difluoromethyl]lithium to vinyl sulfoxides followed by thermal elimination afforded the allylic difluorophosphonates, the products of formal vinylation.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02000-0