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A Novel 1,3-Central-to-Axial Chirality Induction Approach to Cyclooctadiene Lignans
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2003
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Chiral BiarylCatalytic Asymmetric SynthesisCross-coupling ReactionEngineeringCyclooctadiene LignansBiaryl AxisOrganic ChemistryStereoselective SynthesisChemistryHeterocycle ChemistryAsymmetric CatalysisEnantioselective SynthesisBiomolecular Engineering
The catalytic asymmetric synthesis of an axially chiral biaryl, potentially useful intermediate in the synthesis of dibenzocyclooctadiene lignans, has been performed. The key step consisted of a diastereoselective Suzuki coupling between a chiral benzylic alcohol and a sterically hindered boronic ester. The 1,3-induction from the benzylic stereocenter to the biaryl axis proceeded with very good diastereoselectivity.