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Palladium(0) catalyzed 3-aza-cope rearrangement of N-allylenamines

✍ Scribed by Shun-ichi Murahashi; Yoshiki Makabe

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
238 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Pd(0) complexes catalyze the 3-Aza-Cope rearrangement of N-allylenamines to the corresponding 6,c-unsaturated imines or y,+unsaturated carbonyl compounds in the presence of trifluoroacetic acid as co-catalyst. The Cope rearrangements are of considerable synthetic utility. There have been many reports on the attempts to improve the usefulness of aliphatic Claisen rearrangements as a tool for organic synthesis, either by lowering the activation energy of the reaction or by increasing the functionalization of the products. 1 As the former approach transition metal catalyzed rearrangements have been studied extensively, 2-4 and the mechanistic understanding is in progress. 5

We wish to report that N-allylenamines (1) undergo Pd(0) catalyzed 3-Aza-Cope rearrangement to give the corresponding b,c-unsaturated imines (2) in the presence of trifluoroacetic acid as co-catalyst as depicted in eq 1. The 3-Aza-Cope rearrangement is highly useful, because the substrates of N-allyl-

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