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Synthesis 2007(19): 3083-3087
DOI: 10.1055/s-2007-983828
DOI: 10.1055/s-2007-983828
PSP
© Georg Thieme Verlag Stuttgart · New YorkPalladium-Catalyzed Oxidative Aminocarbonylation of Alkynols
Weitere Informationen
Received
2 March 2007
Publikationsdatum:
30. Juli 2007 (online)
Publikationsverlauf
Publikationsdatum:
30. Juli 2007 (online)
Abstract
Alkynols undergo palladium-catalyzed aminocarbonylation leading to the direct formation of different heterocyclic derivatives, depending on the position of the OH group with respect to the triple bond. In the cases of 4-yn-1-ols and (Z)-2-en-4-yn-1-ols, the initially formed 2-ynamide intermediates, respectively, undergo cyclization leading to tetrahydrofuran derivatives or 2-furan-2-ylacetamides, respectively. In the case of 2-yn-1-ols, the aminocarbonylation products undergo intermolecular conjugate addition, followed by lactonization, leading to aminofuranones.
Key words
aminocarbonylation - carbonylations - cyclization - heterocycles - palladium
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