Gold-Catalyzed Oxidative Cyclization of Chiral Homopropargyl Amides: Synthesis of Enantioenriched gamma-Lactams

作者:Shu Chao; Liu Meng Qi; Wang Shan Shan; Li Long; Ye Long Wu*
来源:Journal of Organic Chemistry, 2013, 78(7): 3292-3299.
DOI:10.1021/jo400127x

摘要

A gold-catalyzed tandem cycloisomerization/oxidation of homopropargyl amides has been developed, which provides ready access to synthetically useful chiral gamma-lactams with excellent ee by combining the chiral tert-butylsulfinimine chemistry and gold catalysis. The utility of this methodology has also been demonstrated in the synthesis of biologically active compound S-MPP and natural product (-)-bgugaine. The use of readily available starting materials, a simple procedure, and mild reaction conditions are other significant features of this method.