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Communication | Special issue | Vol 52, No. 3, 2000, pp.1005-1013
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S103
Ligand Effects on the Catalytic Asymmetric Autoinductive Aldol Reaction of 2-TMSOF (2-Trimethylsilyloxyfuran) with Aldehydes

Magali Szlosek, Jean-Christophe Jullian, Reynald Hocquemiller, and Bruno Figadère*

*Laboratoire de Pharmacognosie, associé au CNRS(BIOCIS), Université Paris-Sud, Faculté de Pharmacie, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry Cedex, France

Abstract

We report herein some recent progress in the reaction of 2-TMSOF (2-trimethylsilyloxyfuran) with achiral aldehydes in the presence of a new catalytic system (which does not use the expensive Binol catalyst) yielding the corresponding butenolides with good diastereomeric ratios (d.e. = 90 %) and moderate e.e.’s (50 %).