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Synthesis 2000; 2000(4): 545-548
DOI: 10.1055/s-2000-6372
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TMSOTf-Catalyzed Stereoselective Isomerization of Acetates of the Baylis - Hillman Adducts

Deevi Basavaiah* , Kannan Muthukumaran, Bandaru Sreenivasulu
  • *School of Chemistry, University of Hyderabad, Hyderabad-500046, India
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Publication Date:
31 December 2000 (online)

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TMSOTf-catalyzed isomerization of acetates of the Baylis - Hillman adducts, i.e. methyl 3-acetoxy-3-aryl-2-methylenepropanoates and 3-acetoxy-3-aryl-2-methylenepropanenitriles providing methyl (2E)-2-(acetoxymethyl)-3-arylprop-2-enoates and (2E)-2-(acetoxymethyl)-3-arylprop-2-enenitriles, respectively, is described.

Baylis - Hillman reaction - trimethylsilyl trifluoromethanesulfonate - isomerization - stereoselectivity - 1,2-interaction