Formal alkyne aza-prins cyclization: gold (I)-catalyzed cycloisomerization of mixed N, O-acetals generated from homopropargylic amines to highly substituted …

…, W Jeong, H Kim, V Sampath, YH Rhee

Index: Cheoljae, Kim; Hyo, Jin Bae; Ji, Hyung Lee; Wook, Jeong; Haejin, Kim; Sampath, Vasu; Young, Ho Rhee Journal of the American Chemical Society, 2009 , vol. 131, # 41 p. 14660 - 14661

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Citation Number: 61

Abstract

A new gold (I)-catalyzed cycloisomerization to access highly substituted piperidines has been developed. By combining a conceptually new way of generating iminium ions using cationic gold (I) complexes and an efficient cyclization reaction that can minimize a potentially competing aza-Cope rearrangement, the proposed reaction successfully circumvents a long-standing problem in the classical aza-Prins reaction. Synthetic utility of ...