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  • Title: Gold(I)/Chiral N,N'-Dioxide-Nickel(II) Relay Catalysis for Asymmetric Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement.
    Author: Li J, Lin L, Hu B, Zhou P, Huang T, Liu X, Feng X.
    Journal: Angew Chem Int Ed Engl; 2017 Jan 16; 56(3):885-888. PubMed ID: 27996193.
    Abstract:
    A highly efficient asymmetric cascade reaction between alkynyl esters and allylic alcohols has been realized. Key to success was the combination of a hydroalkoxylation reaction catalyzed by a π-acidic gold(I) complex with a Claisen rearrangement catalyzed by a chiral Lewis acidic N,N'-dioxide-nickel(II) complex. A range of acyclic α-allyl β-keto esters were synthesized in high yields (up to 99 %) with good diastereoselectivities (up to 97:3) and excellent enantioselectivities (up to 99 % ee) under mild reaction conditions. These products can be easily transformed into optically active β-hydroxy esters, β-hydroxy acids, or 1,3-diols.
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