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Synlett 1992; 1992(9): 745-747
DOI: 10.1055/s-1992-21478
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Alkylation Reactions of N-Alkylpyrroles Resulting in the Diastereoselective Formation of Diarylacetic Esters

Martyn J. Earle* , Harry Heaney
  • *Department of Chemistry, The University of Technology, Loughborough, Leicestershire LE11 3TU, England
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Publication Date:
08 March 2002 (online)

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Alkyl α-methoxy- and α-hydroxyheteroarylacetates interact with Lewis acids to give planar cations at different rates, which can lead to a kinetic resolution; the cations can react with a different heterocyclic component to form alkyl diarylacetates such as methyl (N-methyl-3-indolyl)-N-(R)-α-methylbenzyl-2-pyrrylacetate (10) with a diastereofacial selectivity as high as 95%.