Synthesis of axially chiral heterobiaryl alkynes via dynamic kinetic asymmetric alkynylation
2016
Hornillos, Valentín | Ros, Abel | Ramírez-López, Pedro | Iglesias-Sigüenza, Javier | Fernández, Rosario | Lassaletta, José M.
The dynamic kinetic Pd⁰-catalyzed alkynylation of racemic heterobiaryl sulfonates was used for the asymmetric synthesis of axially chiral heterobiaryl alkynes with a broad scope. The use of Pd(OAc)₂/(S)-QUINAP as the precatalyst provides products in excellent yields and enantioselectivities under mild conditions (DMSO, 40 °C). Semireduction, 1,3-dipolar cycladdition or N-oxidation served to illustrate the synthetic potential of the methodology.
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