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Synlett 1995; 1995(3): 269-271
DOI: 10.1055/s-1995-4932
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The Use of a Single Chiral Auxiliary to Generate Different Diastereomeric Diarylacetic Esters

David S. Brown, Martyn J. Earle, Moharem T. El Gihani, Harry Heaney*
  • *Department of Chemistry, The University of Technology, Loughborough, Leicestershire, LE11 3TU
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Publication Date:
31 December 2000 (online)

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Friedel-Crafts reactions of the 8-phenylmethyl α-(N-methyl-3-indolyl)-α-hydroxyacetates with acids in the presence of N-benzylpyrrole gave the expected diarylacetates with a de of >96% via a planar cation; a similar reaction using the 8-phenylmenthyl α-(N-benzyl-2-pyrryl)-α-hydroxyacetates in the presence of N-methylindole gave predominantly the opposite diastereomer (de 82%).

Diastereoselectivity - 8-phenylmenthol - 2-cumylcyclohexanol - oxalylation - Friedel-Crafts - diarylacetate - pyrroles - indoles

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