title: Catalytic enantioselective vinylogous Mukaiyama-Michael addition of 2-silyloxyfurans to cyclic unsaturated oxo esters.
abstract: The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a γ-butenolide or γ-lactone connected to a cycloalkane or cycoalkene moiety.
authors: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, LabEx LERMIT, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors: Xavier
authors: X
authors: Jusseau
authors: Pascal
authors: P
authors: Retailleau
authors: Laurent
authors: L
authors: Chabaud
authors: Catherine
authors: C
authors: Guillou
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007783:Lactones; D003300:Copper; C004511:butenolide; D015107:4-Butyrolactone