Formal Alkyne Aza-Prins Cyclization: Gold(I)-Catalyzed Cycloisomerization of Mixed N,O-Acetals Generated from Homopropargylic Amines to Highly Substituted Piperidines
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- 作者：Cheoljae Kim ; Hyo Jin Bae ; Ji Hyung Lee ; Wook Jeong ; Haejin Kim ; Vasu Sampath ; Young Ho Rhee
- 刊名：Journal of the American Chemical Society
- 出版年：2009
- 出版时间：October 21, 2009
- 年：2009
- 卷：131
- 期：41
- 页码：14660-14661
- 全文大小：192K
- 年卷期：v.131,no.41(October 21, 2009)
- ISSN：1520-5126
文摘
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 the catalytic reaction was demonstrated by a synthesis of optically active 2-alkyl-piperidin-4-one.