One-step RhCl3-catalyzed deprotection of acyclic N-allyl amides.
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.
Zacuto
Michael J
MJ
Department of Process Research, Merck Research Laboratory, Rahway, NJ 07065, USA. michael_zacuto@merck.com
Xu
Feng
F
D000438:Alcohols; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D008956:Models, Chemical; D012238:Rhodium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013997:Time Factors
D000438:Alcohols; D000577:Amides; D012997:Solvents; D012238:Rhodium