Reactivity of cyclic sulfamidates towards phosphonate-stabilised enolates: synthesis and applications of alpha-phosphono lactams

Five and six ring alpha- phosphono lactams 14 - 20 are available by reaction of 1,2- and 1,3- cyclic sulfamidates respectively with enolates derived from ethyl dialkylphosphonoacetates 3 and 4. Subsequent Wadsworth - Emmons olefination provides the enantiomerically pure exo- alkylidene variants e. g...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 5; no. 16; pp. 2636 - 2644
Main Authors Bower, John F., Williams, Andrew J., Woodward, Hannah L., Szeto, Peter, Lawrence, Ron M., Gallagher, Timothy
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2007
Subjects
Chemistry
Chemistry, Organic
Cyclization
Ketones - chemistry
Lactams - chemical synthesis
Lactams - chemistry
Molecular Structure
Organophosphonates - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Sulfonamides - chemistry
REAGENTS
(-)-APHANORPHINE
PRECURSORS
C-H INSERTION
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Summary:Five and six ring alpha- phosphono lactams 14 - 20 are available by reaction of 1,2- and 1,3- cyclic sulfamidates respectively with enolates derived from ethyl dialkylphosphonoacetates 3 and 4. Subsequent Wadsworth - Emmons olefination provides the enantiomerically pure exo- alkylidene variants e. g. 25, which is efficiently converted to vinyl triflate 29 (> 98% ee). Suzuki coupling of 29 to a range of aryl and vinyl boronic acids leads to a structurally diverse range of pyrrolidinones exemplified by 30 and 34. The degree of epimerisation at the base- sensitive C( 5) stereocentre during the Suzuki coupling of 29 is shown to be dependent on both the nature of the aryl boronic acid and the reaction conditions used.
ISSN:1477-0520
DOI:10.1039/b706315f