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Issue 1, 1985
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Kinetics and stereochemistry of β-elimination of (S)-O-acylthreonine in Λ- and Δ-bis-[N-salicylidene-(S)-O-acylthreoninato]cobaltate(III) ions. Implications for vitamin B6-catalysed reactions

Yurii N. Belokon,  Ashot S. Sagiyan,  Irina V. Ponomarenko,  Vladimir I. Bakhmutov  and  Vasilii Belikov 

Abstract

Diastereoisomeric complexes of Λ- and Δ-bis-[N-3-R′-salicylidene-(S)-O-acylthreoninato]cobaltate(III) have been synthesized. Deacylation of the complexes at 25 °C and pH 9–11.0 yields a mixture of isomeric Λ- and Δ-bis-(N-3-R′-salicylidene-α-aminodehydrobutyrato)cobaltate(III) ions. Deacylation is subject to general base catalysis. A comparison of the rate constants for epimerization of Λ- and Δ-bis-[N-3-R′-salicylidene-(S)-threoninato]cobaltate(III) ions with those for deacylation of their acyl derivatives shows that deacylation follows the (E1 cB)I mechanism. The ratio of the products formed via the syn- or anti-elimination mechanism depends on the nature of the base which catalyses the process. The neutral base DABCO catalyses syn-elimination predominantly whereas the negatively charged carbonate ion brings about anti-elimination. The stereochemistry of pyridoxal-dependent reactions of β-elimination has been discussed along the lines of the data obtained.

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Article type: Paper
DOI: 10.1039/P29850000021
Citation: J. Chem. Soc., Perkin Trans. 2, 1985,0, 21-27
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    Kinetics and stereochemistry of β-elimination of (S)-O-acylthreonine in Λ- and Δ-bis-[N-salicylidene-(S)-O-acylthreoninato]cobaltate(III) ions. Implications for vitamin B6-catalysed reactions

    Y. N. Belokon, A. S. Sagiyan, I. V. Ponomarenko, V. I. Bakhmutov and V. Belikov, J. Chem. Soc., Perkin Trans. 2, 1985, 0, 21
    DOI: 10.1039/P29850000021

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