Gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides: a reliable access to enantioenriched pyrrolidin-3-ones.
A gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides has been developed, which provides a reliable access to synthetically useful chiral pyrrolidin-3-ones with excellent ee, by combining the chiral tert-butylsulfinimine chemistry and gold catalysis. This methodology has also been used in the facile synthesis of natural product (-)-irniine. The use of readily available starting materials, a broad substrate scope, a simple procedure and the mild nature of this reaction render it a viable alternative for the synthesis of enantioenriched pyrrolidin-3-ones.
State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, Fujian, PR China. longwuye@xmu.edu.cn.
Chao
C
Shu
Long
L
Li
Yong-Fei
YF
Yu
Shuang
S
Jiang
Long-Wu
LW
Ye
D000470:Alkaloids / Q000138:chemical synthesis*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis*; D011760:Pyrrolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D000470:Alkaloids; D011759:Pyrrolidines; D011760:Pyrrolidinones; D013449:Sulfonamides; C411262:irniine; D006046:Gold