α, β??Unsaturated δ??Lactones from Copper??Catalyzed Asymmetric Vinylogous Mukaiyama Reactions of Aldehydes: Scope and Mechanistic Insights

B Bazán??Tejeda, G Bluet, G Broustal…

Index: Bazan-Tejeda, Belen; Bluet, Guillaume; Broustal, Garance; Campagne, Jean-Marc Chemistry - A European Journal, 2006 , vol. 12, # 32 p. 8358 - 8366

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Citation Number: 39

Abstract

Abstract A direct regio-, diastereo-, and enantiocontrolled access to α, β-unsaturated δ- 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.