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Issue 23, 1999
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Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes

Abstract

The synthesis of (SRSS )-[(phenylsulfinyl)benzene] chromium tricarbonyl 5 and (SRSS )-[( p-tolylsulfinyl)benzene] chromium tricarbonyl 6 is achieved via a nucleophilic displacement reaction between the anion derived from (benzene) chromium tricarbonyl 9 and a suitable sulfinate ester. Replacing the sulfinate ester with a chiral sulfinyl-transfer reagent allows the isolation of the non-racemic sulfinyl-substituted complexes with good enantioselectivities (ee 80–89%) under optimised conditions. The use of Kagan’s cyclic sulfite methodology for the synthesis of an enantiomerically pure tert-butylsulfinyl complex is unsuccessful, but results in the identification of a novel fragmentation–isomerisation process of the intermediate sulfinate.

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Article type: Paper
DOI: 10.1039/A907590I
Citation: J. Chem. Soc., Perkin Trans. 1, 1999,0, 3405-3412
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    Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes

    S. G. Davies, T. Loveridge, M. Fatima C. C. Teixeira and J. M. Clough, J. Chem. Soc., Perkin Trans. 1, 1999, 0, 3405
    DOI: 10.1039/A907590I

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