doi: 10.1021/jo070553t.
Epub 2007 Jul 11.
One-step RhCl3-catalyzed deprotection of acyclic N-allyl amides
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- PMID: 17625881
- DOI: 10.1021/jo070553t
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One-step RhCl3-catalyzed deprotection of acyclic N-allyl amides
J Org Chem.
.
Abstract
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.
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