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The reactivity of 5-methyl-4-(pyrrolidin-1-yl)-5H-furan-2-one with aldehydes and with acyl chlorides followed by reduction was studied. The aldol condensation gave predominantly the anti aldol product when the acylation-reduction sequence led exclusively to the syn product. The use of a chiral pyrrolidine, (S)-2-methoxymethylpyrrolidine (SMP), allowed the synthesis of enantio-enriched compounds, the acylation-reduction leading to the (R,R) addition product.
UMR 8638 CNRS/Université René Descartes, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 4 avenue de l'Observatoire, 75270 Paris Cedex 06, France
UMR 8638 CNRS/Université René Descartes, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 4 avenue de l'Observatoire, 75270 Paris Cedex 06, France
UMR 8015 CNRS/Université René Descartes, Laboratoire de Cristallographie et RMN Biologiques, Faculté de Pharmacie, 4 avenue de l'Observatoire, 75270 Paris Cedex 06, France
UMR 8638 CNRS/Université René Descartes, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 4 avenue de l'Observatoire, 75270 Paris Cedex 06, France