Concise Synthesis of Enantiomerically Pure (1'S,2'R)- and (1'R,2'S)-2S-Amino-3-(2'-aminomethyl-cyclopropyl)propionic Acid: Two E-Diastereoisomers of 4,5-Methano-l-lysine

Timothy Altamore, Oanh Nguyen, Quentin Churches, Kate Cavanagh, Xuan Nguyen, Sandhya Duggan, Guy Krippner, Peter Duggan

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    A concise synthesis of both E-isomers of 2S-amino-3-(2′-aminomethyl- cyclopropyl)propionic acid, new methano-l-lysines, is described. The synthetic route includes nine steps from l-methionine, with a key step involving the cyclopropanation of an intermediate E-allylic alcohol. The resultant hydroxymethylcyclopropanes were readily separated and converted into the title α-amino acids. The stereochemistry around the cyclopropane rings was deduced by conducting the cyclopropanation in the presence of N,N,N′,N′-tetramethyl-d-tartaric acid diamide butylboronate, a chiral controller which is known to favour the production of S-hydroxymethyl cyclopropanes from allylic alcohols.

    Original languageEnglish
    Pages (from-to)1105-1111
    Number of pages7
    JournalAustralian Journal of Chemistry
    Issue number9
    Publication statusPublished - 2013


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