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■ Yb(OTf)₃-catalyzed Vinylogous Mannich Reaction of Trialkylsilyloxyfuran

Sylvain Oudeyer, Bruno Dudot, and Jacques Royer*

*CNRS-University Paris5, Faculty of Pharmacy, 4 avenue de l’Observatoire, 75270 Paris Cedex 06, France

Abstract

The one-pot three-component vinylogous Mannich reaction of trialkylsilyloxyfurans with anilines and aldehydes in the presence of catalytic amounts of Yb(OTf)₃ gave the substituted aminoalkyl-butenolides in good yields (> 90 %) and diastereoselectivities (d.e. > 60 %). The configuration of the major product is erythro (anti) and was confirmed by chemical transformation into piperidinone derivatives and ¹H NMR spectral studies of the latter compounds. The vinylogous Mannich reaction performed with preformed imines proceeded similarly with a preferred erythro selectivity while the condensation of 3-methyl-2-trialkylsilyloxyfurans was threo selective.