title: Enantioselective synthesis of hindered cyclic dialkyl ethersviacatalytic oxa-Michael/Michael desymmetrization.
abstract: An asymmetric oxa-Michael/Michael cascade reaction ofp-quinols and α,β-unsaturated aldehydes provides access to hindered dialkyl ethers. A highly enantioselective oxa-Michael addition of a tertiary alcohol precedes an intramolecular cyclohexadienone desymmetrization, which allows for the concomitant formation of four contiguous stereocenters in a single step. The highly functionalized bicyclic frameworks are rapidly obtained from simple starting materials with good diastereoselection and serve as valuable precursors for further manipulation.
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: Michael T
authors.initials: MT
authors.lastname: Corbett
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson