Formal alkyne aza-prins cyclization: gold(I)-catalyzed cycloisomerization of mixed N,O-acetals generated from homopropargylic amines to highly substituted piperidines.
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.
Kim
Cheoljae
C
Department of Chemistry, POSTECH (Pohang University of Science and Technology), Hyoja-dong San 31, Pohang, Kyungbuk, Republic of Korea 790-784.
Bae
Hyo Jin
HJ
Lee
Ji Hyung
JH
Jeong
Wook
W
Kim
Haejin
H
Sampath
Vasu
V
Rhee
Young Ho
YH
D000080:Acetals / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D010880:Piperidines / Q000737:chemistry*
D000080:Acetals; D000480:Alkynes; D000588:Amines; D001372:Aza Compounds; D010880:Piperidines; D006046:Gold