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Synlett 1993; 1993(5): 323-332
DOI: 10.1055/s-1993-22443
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Arene Chromium Tricarbonyl Stabilised Benzylic Carbocations

Stephen G. Davies* , Timothy J. Donohoe
  • *The Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, England
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Publication Date:
19 March 2002 (online)

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The ability of the chromium tricarbonyl unit to stabilise benzylic carbocations and oxonium ions is described. We have investigated the use of arene chromium tricarbonyl complexes as chiral auxiliaries for asymmetric synthesis. The synthesis of homochiral tetrahydroisoquinolines, tetrahydrobenzazepines, and 2-aryltetrahydropyrans via intramolecular cyclisation of a nucleophile onto chromium tricarbonyl stabilised benzylic carbocations and oxonium ions is described. 1. Introduction 2. Evidence for the Chromium Tricarbonyl Stabilisation of Benzylic Carbocations 3. Acyclic Systems without ortho Substitution 3.1 Carbocations 3.2 Oxonium Ions 4. Bicyclic Complexes 4.1 (6-5) Ring Systems 4.2 (6-6) Ring Systems 5. ortho Substituted Acyclic Compounds 5.1 Carbocations 5.2 Oxonium Ions 6. Miscellaneous Applications of Chromium Tricarbonyl Stabilised Carbocations

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