Chiral Phosphoric Acid-Catalyzed Enantioselective Dearomative Spirocyclization of Phenol-Ynamides by Kinetic
Jia-Tian Jiang1, Pei-Yuan Zhang1, Hua-Hong Chen1
1Fujian Key Laboratory of Chemical Biology and State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Abstract:
Chiral spirocycles are the core structures of many biologically important compounds. Due to the difficulties in constructing quaternary carbon stereocenters, the synthesis of chiral spirocycles is challenging. Herein, we report a chiral phosphoric acid (CPA)-catalyzed enantioselective dearomative spirocyclization of phenol-ynamides by kinetic resolution, leading to the atom-economical synthesis of various enantioenriched spiro[4.5]decan-6-one derivatives with high enantioselectivities. This protocol represents an important advancement in metal-free enantioselective dearomatization of phenols with alkynes.
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