Journal
TETRAHEDRON LETTERS
Volume 59, Issue 9, Pages 848-852Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.01.058
Keywords
Ugi reaction; Dehydroalanines; Palladium catalysis; 1,4-and 1,5-olefin migration; beta-Amino elimination
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Funding
- Marcos Moshinsky Foundation
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1,4- or 1,5-migration of a double bond of dehydroalanines under palladium catalysis is reported. The process occurred with several highly-substituted dehydroalanines under mild typical Heck reaction conditions. Although this was one of the first reports of a palladium-catalyzed 1,5-olefin migration, the outcome of the reaction was susceptible to the starting material. Mechanistically, the process involved a five- (1,4-migration) or six-membered ring (1,5-migration) organopalladium intermediate, which cleaved a C-N bond in an beta-amino elimination process. (C) 2018 Elsevier Ltd. All rights reserved.
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