Cooperative Catalysis for the Highly Diastereo‐ and Enantioselective [4+3]‐Cycloannulation of <i>ortho</i>‐Quinone Methides and Carbonyl Ylides
Arun Suneja, Henning Jakob Loui, Christoph Schneider
Abstract
We describe herein a highly diastereo- and enantioselective [4+3]-cycloannulation of ortho-quinone methides and carbonyl ylides to furnish functionalized oxa-bridged dibenzooxacines with excellent yields and stereoselectivity in a single synthetic step. The combination of rhodium and chiral phosphoric acid catalysis working in concert to generate both transient intermediates in situ provides direct access to complex bicyclic products with two quaternary and one tertiary stereogenic centers. The products may be further functionalized into valuable and enantiomerically highly enriched building blocks.
Topics & Concepts
StereocenterEnantioselective synthesisChemistryCatalysisRhodiumOrganocatalysisQuinonePhosphoric acidCombinatorial chemistryBicyclic moleculeOrganic chemistryStereochemistrySynthesis of Indole DerivativesCarbohydrate Chemistry and SynthesisSulfur-Based Synthesis Techniques