A Versatile Chemo-Enzymatic Route to Enantiomerically Pure β-Branched α-Amino Acids

Geoffrey J. Roff, Richard C. Lloyd, Nicholas J. Turner

    Research output: Contribution to journalArticlepeer-review

    Abstract

    A series of diastereoisomers of β-methyl-β-phenylalanine analogues 1a?f have been prepared in enantiomerically pure form using a combination of chemo- and biocatalysis. Starting from l-threonine methyl ester 2, a range of β,β-disubstituted didehydroamino acids were obtained as their (Z)-isomers 6a?f. Asymmetric hydrogenation of these alkenes, using either the [Rh(R,R)-Et-DuPhos(COD)]BF4 or [Rh(S,S)-Et-DuPhos(COD)]BF4 catalyst, followed by hydrolysis yielded two of the four possible sets of diastereoisomers of the β-branched amino acid. Subsequent stereoinversion, using a stereoselective amino acid oxidase in combination with a nonselective reducing agent, furnished the remaining two sets of diastereomers. Copyright © 2004 American Chemical Society.
    Original languageEnglish
    Pages (from-to)4098-4099
    Number of pages1
    JournalJournal of the American Chemical Society
    Volume126
    Issue number13
    DOIs
    Publication statusPublished - 7 Apr 2004

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