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Title

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

AuthorsBoto, Alicia ; Hernández, Rosendo ; Suárez, Ernesto
Issue Date7-Jul-2000
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 65(16): 4930-4937 (2000)
AbstractA 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.
Description8 pages, 2 tables, 5 schemes.-- PMID: 10956474 [PubMed].-- Printed version published Aug 11, 2000.
Publisher version (URL)http://dx.doi.org/10.1021/jo000356t
URIhttp://hdl.handle.net/10261/13547
DOI10.1021/jo000356t
ISSN0022-3263
Appears in Collections:(IPNA) Artículos
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