Efficient synthesis of protected cyclopropyl β-aspartylphosphates

Luke A. Adams, Jonathan P H Charmant, Russell J. Cox, Magnus Walter, William G. Whittingham

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19 Citations (Scopus)


The in situ reaction of protected dehydroamino acids with derivatives of vinyldiazomethane leads to good to excellent yields of vinyl cyclopropanes via 3 + 2 dipolar cycloaddition followed by N 2 extrusion. Chromatographic separation of the cyclopropane diastereomeric products, followed by characterisation by 1H NMR and X-ray crystallography allowed the cis and trans diastereomers to be easily identified. Oxidative cleavage of the vinyl moiety then led directly to protected cyclopropane aspartic acid derivatives in three steps from commercially available materials. These compounds were converted to protected methylenephosphonate, difluoromethylenephosphonate and phosphoramidate analogues of β-aspartyl phosphate.

Original languageEnglish
Pages (from-to)542-553
Number of pages12
JournalOrganic & Biomolecular Chemistry
Issue number4
Publication statusPublished - 21 Feb 2004

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