Tetrahedron Letters p. 2449 - 2452 (1985)
Update date:2022-08-03
Topics:
Minami, Ichiro
Ohashi, Yukihiro
Shimizu, Isao
Tsuji, Jiro
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.
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