1191953-06-6Relevant articles and documents
Formal alkyne aza-prins cyclization: Gold(I)-catalyzed cycloisomerization of mixed N,O-acetals generated from homopropargylic amines to highly substituted piperidines
Cheoljae, Kim,Hyo, Jin Bae,Ji, Hyung Lee,Wook, Jeong,Haejin, Kim,Sampath, Vasu,Young, Ho Rhee
supporting information; scheme or table, p. 14660 - 14661 (2010/02/28)
(Chemical Equation Presented). 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.
