Au(I)-catalyzed rearrangement reaction of propargylic aziridine: synthesis of trisubstituted and cycloalkene-fused pyrroles.
A rearrangement reaction of propargylic aziridine, catalyzed by PPh(3)AuCl/AgOTf, forming trisubstituted and cycloalkene-fused pyrroles is described which involves an unusual tandem cyclization/ring-opening/Wagner-Meerwein process. The unique structures of the products demonstrated its potential applications for synthesizing structurally diverse alkaloids.
Zhao
Xiong
X
State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.
Zhang
En
E
Tu
Yong-Qiang
YQ
Zhang
Yong-Qiang
YQ
Yuan
Dao-Yi
DY
Cao
Ke
K
Fan
Chun-An
CA
Zhang
Fu-Min
FM
D000480:Alkynes / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D017612:Gold Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001388:Aziridines; D017612:Gold Compounds; D011758:Pyrroles; C033132:aziridine