PALLADIUM-CATALYZED REACTION OF ALLYL CARBAMATES; ALLYLATION OF CARBONUCLEOPHILES, AND PROTECTION-DEPROTECTION OF AMINES

Article abstract of DOI:10.1016/S0040-4039(00)94850-0

Allylation of carbonucleophiles with allylic carbamates under neutral conditions has been studied.The C-allylation of carbonucleophile is competitive with the N-allylation of amines, and the structure of amines is crucial for the selectivity.Bulky secondary amines gave the best results.Also a new method of protection-deprotection of amines as carbamates has been developed.Smooth deprotection is possible by the palladium-catalyzed reaction of allyl carbamates with formic acid.This method is particulary useful for primary amines, including optically active amino acids.