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Synlett 1990; 1990(6): 333-334
DOI: 10.1055/s-1990-21082
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Asymmetric and Stereoselective Cycloaddition of the Acrylate and Fumarate of (R)-Methyl Mandelate to α-Hydroxy-o-quinodimethane

James L. Charlton* , Kevin Koh
  • *Department of Chemistry, University of Manitoba, Winnipeg, Canada R3T 2N2
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Publication Date:
08 March 2002 (online)

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The cycloaddition of α-hydroxy-o-quinodimethane, generated photochemically from 2-methylbenzaldehyde, and thermally from 1-benzocyclobutenol or 1-hydroxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide, with the fumarate and acrylate of (R)-methyl mandelate proceeds with high asymmetric induction and stereoselectivity (>90% de) to give 1-hydroxy-1,2,3,4-tetrahydronaphthalene derivatives in moderate to excellent yield.