Alpha,beta-unsaturated delta-lactones from copper-catalyzed asymmetric vinylogous Mukaiyama reactions of aldehydes: scope and mechanistic insights.
A direct regio-, diastereo-, and enantiocontrolled access to alpha,beta-unsaturated delta-lactones is described, based on the reaction of a silyl dienolate and an aldehyde in the presence of 10 % of Carreira's catalyst. The scope and limitations of this reaction, as well as mechanistic insights concerning the reactivity of an allyl copper species, are discussed.
Bazán-Tejeda
Belén
B
Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Bluet
Guillaume
G
Broustal
Garance
G
Campagne
Jean-Marc
JM
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D008956:Models, Chemical; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D007783:Lactones; D009942:Organometallic Compounds; D012821:Silanes; D003300:Copper