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Atroposelective Synthesis of Axially Chiral Biaryls by Palladium‐Catalyzed Asymmetric C−H Olefination Enabled by a Transient Chiral Auxiliary
101
Citations
69
References
2017
Year
Atroposelective SynthesisEngineeringTransient Chiral AuxiliaryChiral BiarylsAxially Chiral BiarylsOrganic ChemistryCatalysisDemanding SubstituentsChemistryStereoselective SynthesisExcellent SelectivityAsymmetric CatalysisEnantioselective SynthesisBiomolecular Engineering
Abstract Atroposelective synthesis of axially chiral biaryls by palladium‐catalyzed C−H olefination, using tert ‐leucine as an inexpensive, catalytic, and transient chiral auxiliary, has been realized. This strategy provides a highly efficient and straightforward access to a broad range of enantioenriched biaryls in good yields (up to 98 %) with excellent enantioselectivities (95 to >99 % ee ). Kinetic resolution of trisubstituted biaryls bearing sterically more demanding substituents is also operative, thus furnishing the optically active olefinated products with excellent selectivity (95 to >99 % ee , s ‐factor up to 600).
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