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Issue 8, 1994
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Kinetic resolution of the chiral iron acetyl complexes [Fe(CO)(η5-C5H5)(L)COCH3][L = PPh3, P(p-tolyl)3]via aldol reactions with camphor

Abstract

The chiral iron acetyl complexes [Fe(CO)(η5-C5H5)(L)COCH3][L = PPh3, P(p-tolyl)3] have been kinetically resolved via aldol reactions involving their derived lithium enolates and camphor in the presence of lithium chloride. With (1R)-(+)-camphor the faster reacting iron acetyl enantiomer had the (S)-configuration allowing the (R)-iron acetyls to be obtained after recovery of starting material and crystallisation. The corresponding (S)-iron acetyls can be obtained by a base-promoted reverse aldol reaction of the isolated products. A mechanistic rationale for the high enantiomeric discrimination is proposed which involves a chelation-controlled chair transition state with a disfavourable 1-methyl to cyclopentadienyl interaction in the mismatched pairing.

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Article type: Paper
DOI: 10.1039/P19940000933
Citation: J. Chem. Soc., Perkin Trans. 1, 1994,0, 933-941
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    Kinetic resolution of the chiral iron acetyl complexes [Fe(CO)(η5-C5H5)(L)COCH3][L = PPh3, P(p-tolyl)3]via aldol reactions with camphor

    S. C. Case-Green, J. F. Costello, S. G. Davies, N. Heaton, C. J. R. Hedgecock, V. M. Humphreys, M. R. Metzler and J. C. Primes, J. Chem. Soc., Perkin Trans. 1, 1994, 0, 933
    DOI: 10.1039/P19940000933

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