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Tandem radical decarboxylation-oxidation of amino acids: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping

AutorBoto, Alicia ; Hernández, Rosendo ; Suárez, Ernesto
Fecha de publicación7-jul-2000
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 65(16): 4930-4937 (2000)
ResumenA convenient methodology for the synthesis of 2-substituted pyrrolidines from α-amino acids is described. A number of cyclic and acyclic α-amino acid derivatives have been prepared in order to test the scope and diastereoselectivity of this method. These substrates were treated with iodosylbenzene or (diacetoxyiodo)benzene (DIB) and iodine in order to generate the corresponding carboxyl radical, which evolves by loss of carbon dioxide to produce a carbon radical which in turn undergoes oxidation to an N-acyliminium ion. This postulated intermediate could be trapped inter- or intramolecularly by oxygen, nitrogen and carbon nucleophiles. In the case of carbon nucleophiles, a Lewis acid is required for the concomitant carbon−carbon bond formation. High yields and modest diastereoselectivities were obtained. The present methodology was applied to the synthesis of ω-amino aldehydes or hemiaminals 8−14, 2-aminopyrrolidine derivative 15, aminolactone derivative 16, and azasugar analogues 17 and 18. When carbon nucleophiles were used, alkaloid precursors such as 2-allyl- or 2-alkylpyrrolidines 19−23 and 25 were obtained.
Descripción8 pages, 2 tables, 5 schemes.-- PMID: 10956474 [PubMed].-- Printed version published Aug 11, 2000.
Versión del editorhttp://dx.doi.org/10.1021/jo000356t
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