One-pot synthesis of fused pyrroles through a key gold-catalysis-triggered cascade.
A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields.
Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93117 (USA).
Zhitong
Z
Zheng
Huangfei
H
Tu
Liming
L
Zhang
D064751:Ammonium Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D064751:Ammonium Compounds; D011083:Polycyclic Compounds; D011758:Pyrroles; D006046:Gold
catalysis; gold; hydroxamines; pyrroles; rearrangement