(1R)-(+)-Camphor and Acetone Derived α′-Hydroxy Enones in Asymmetric Diels−Alder Reaction: Catalytic Activation by Lewis and Brønsted Acids, Substrate Scope, Applications in Syntheses, and Mechanistic Studies

摘要: The Diels−Alder reaction constitutes one of the most powerful and convergent C−C bond-forming transformations continues to be privileged route access cyclohexene substructures, which are widespread within natural products bioactive constituents. Over recent years, asymmetric catalytic methodologies have experienced a tremendous advance, but still inherently difficult diene-dienophile combinations prevail, such as those involving dienes less reactive than cyclopentadiene or dienophiles like β-substituted acrylates equivalents. Here main features α′-hydroxy enones partners shown, with especial focus on their potentials limitations in solving above cases. α′-Hydroxy able bind reversibly both Lewis acids Bronsted acids, forming 1,4-coordinated species that shown efficiently engage these reactions. On bases, convenient control rea...