One-Step RhCl3-Catalyzed Deprotection of Acyclic N-Allyl Amides
摘要:
[GRAPHICS]A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Preliminary mechanistic studies reveal that the key to the success of the one-step deprotection process is the dual function of RhCl3 in alcohol solvents. Reaction of RhCl3 with n-PrOH not only provides an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides but also generates a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.
ANFINOGENOV V. A.; FILIMONOV V. D.; SIROTKINA E. E., ZH. ORGAN. XIMII, 1978, 14, HO 8, 1723-1729
作者:ANFINOGENOV V. A.、 FILIMONOV V. D.、 SIROTKINA E. E.
DOI:——
日期:——
One-Step RhCl<sub>3</sub>-Catalyzed Deprotection of Acyclic <i>N</i>-Allyl Amides
作者:Michael J. Zacuto、Feng Xu
DOI:10.1021/jo070553t
日期:2007.8.1
[GRAPHICS]A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Preliminary mechanistic studies reveal that the key to the success of the one-step deprotection process is the dual function of RhCl3 in alcohol solvents. Reaction of RhCl3 with n-PrOH not only provides an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides but also generates a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.
FILIMONOV V. D.; ANFINOGENOV V. A.; SIROTKINA E. E., XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 4, 497-502
作者:FILIMONOV V. D.、 ANFINOGENOV V. A.、 SIROTKINA E. E.