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One-Step RhCl3-Catalyzed Deprotection of Acyclic N-Allyl Amides

Michael J. Zacuto* and Feng Xu

*Department of Process Research, Merck Research Laboratory, Rahway, New Jersey 07065, Email: michael_zacutomerck.com

M. J. Zacuto, F. Xu, J. Org. Chem., 2007, 72, 6298-6300.

DOI: 10.1021/jo070553t (free Supporting Information)


Abstract

A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Reactions of RhCl3 with n-PrOH provide an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides and generate a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.

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Key Words

deprotection


ID: J42-Y2007-2610