Chiral metal complexes. 18. A highly stereoselective synthesis of alanine

Terence J. Goodwin, Mohammed W. Mulqi, Peter A. Williams*, Robert S. Vagg

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    Abstract

    The complex Λ-β1-[Co(R,R-picchxn)(AMMAH)](ClO4)2·4 1 2H2O, where R,R-picchxn is N,N′-di(2picolyl)-1R,2R-diaminocyclohexane and AMMAH2 is 2-amino-2-methylpropandioic acid has been prepared stereospecifically from the reaction of Λ-β-[Co(R,Rpicchxn)Cl2]+ and AMMAH2 is aqueous solution. Decarboxylation of the complex in aqueous HCl under a variety of conditions always gave the mixture of diastereoisomers containing R-alanine and S-alanine in the same ratio, Λ-β1-[Co(R,R-picchxn)(R-ala)]2+: Λ-β1-[Co(R,R-picchxn)(S-ala)]2+ = 89 ± 0.5: 11 ± 0.5. The optical yield of alanine is the highest ever achieved in this kind of reaction.

    Original languageEnglish
    Pages (from-to)141-146
    Number of pages6
    JournalInorganica Chimica Acta
    Volume98
    Issue number3
    DOIs
    Publication statusPublished - 1 Apr 1985

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