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Issue 4, 1997
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Chiral base mediated asymmetric synthesis of tricarbonyl(η6-arene)chromium complexes

Abstract

Enantiomerically enriched tricarbonyl(η6-arene)chromium complexes can be obtained in up to 94% ee from the enantioselective ortho-metallation reaction of certain symmetrically substituted complexes with Me3SiCl, mediated by a chiral lithium amide base. The level of asymmetric induction depends upon the nature of the starting ring substituent(s) and, in the case of anisole-type complexes, a proton transfer reaction involving the chiral metallated intermediate and the neutral tricarbonyl(η6-arene)chromium complex results in rapid racemisation in the absence of an in situ electrophilic quench. Non-racemic derivatives of a tricarbonyl(η6-arene)chromium complex derived from 1,3-dihydroisobenzofuran are also prepared in up to 99% ee by chiral base deprotonation, and trends in the regioselectivity of metallation of this complex with a range of lithium amide bases are described.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1997, 401-416
Article type
Paper

Chiral base mediated asymmetric synthesis of tricarbonyl(η6-arene)chromium complexes

R. A. Ewin, A. M. MacLeod, D. A. Price, N. S. Simpkins and A. P. Watt, J. Chem. Soc., Perkin Trans. 1, 1997, 401
DOI: 10.1039/A605812D

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