Water-promoted one-pot vinylogous Mannich-type reaction of trimethylsilyloxyfuran

G Landelle, A Claraz, S Oudeyer, V Levacher

Index: Landelle, Gregory; Claraz, Aurelie; Oudeyer, Sylvain; Levacher, Vincent Tetrahedron Letters, 2012 , vol. 53, # 19 p. 2414 - 2416

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Citation Number: 9

Abstract

Water, produced in situ during the formation of imines from aldehydes 1 and amines 2, is employed to promote the one-pot Mannich reaction of trimethylsilyloxyfuran 3a without addition of extra solvent or catalyst. This clean and quick reaction allows the obtention of a series of 5-substituted γ-butenolides 4 with good yields and modest diastereomeric ratio. A large panel of substituents is tolerated ranging from aliphatic chains to aromatic or ...