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Synlett 1996; 1996(8): 747-748
DOI: 10.1055/s-1996-5524
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Unprecedented Stereochemical Reversal from Alkyl to Aryl Substituents in the Johnson-Claisen Rearrangement of Methyl 3-Hydroxy-2-methylenealkanoates

D. Basavaiah* , S. Pandiaraju, M. Krishnamacharyulu
  • *School of Chemistry, University of Hyderabad, Hyderabad-500 046, India
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Publication Date:
31 December 2000 (online)

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An unprecedented stereochemical reversal from alkyl to aryl substituents in the Johnson-Claisen rearrangement of methyl 3-hydroxy-2-methylenealkanoates with triethyl orthoacetate with a plausible mechanism has been described.

The Johnson-Claisen rearrangement - the Baylis-Hillman reaction - methyl 3-hydroxy-2-methylenealkanoates - (Z)- and (E)-alk-4-enoates

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