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Synlett 1996; 1996(4): 317-318
DOI: 10.1055/s-1996-5423
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Regioselective and Enantioselective Metallation of A Tricarbonyl(η6-arene)chromium Complex Derived from 1,3-Dihydroisobenzofuran

Richard A. Ewin, Nigel S. Simpkins*
  • *Department of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, UK, Fax (0115) 9513564; e-mail Nigel.Simpkins@Nottingham.ac.uk
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Publication Date:
31 December 2000 (online)

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The tricarbonyl(η6-arene)chromium complex derived from 1,3-dihydroisobenzofuran (phthalan) can be converted into chiral non-racemic derivatives, in up to 80% ee, via asymmetric deprotonation at the benzylic position using a chiral lithium amide base. Unexpectedly, different alkyllithium and lithium amide bases showed contrasting regioselectivities in deprotonation of the phthalan complex at either the benzylic or ortho positions.

enantioselective metallation - chiral lithium amide - tricarbonyl(η6-arene)chromium complex