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Direct conversion of allylic selenides to protected allylic amines

โœ Scribed by Shea, Regan G.; Fitzner, Jeffrey N.; Fankhauser, John E.; Hopkins, Paul B.

Book ID
126076387
Publisher
American Chemical Society
Year
1984
Tongue
English
Weight
541 KB
Volume
49
Category
Article
ISSN
0022-3263

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โœ John E. Fankhauser; Richard M. Peevey; Paul B. Hopkins ๐Ÿ“‚ Article ๐Ÿ“… 1984 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 230 KB

Anhydrous chloramine T in methanol is a highly effective reagent for the conversion of allylic phenyl selenides to the corresponding rearranged N-allylic-p-toluenesulfonamides. The reaction presumably proceeds via an allylic selenimide intermediate which undergoes [2,3]sigmatropic rearrangement. The

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Synthesis of potential antiparisitic 5'-aminonucloesides such as 10 could not be accomplished using standard amination procedures. Palladium(0)-catalyzed amination of cyclic allylic acetates with benzylamine or phthalimide gave the corresponding protected amines. This method was then extended to the