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Title

Synthesis of alkaloids from aminol derivatives by β-fragmentation of primary alkoxyl radicals

AuthorsBoto, Alicia CSIC ORCID ; Hernández, Rosendo CSIC; Montoya, Adriana; Suárez, Ernesto CSIC ORCID
KeywordsRadicals
Alkaloids
Acyliminium ions
Fragmentation
Nucleophilic addition
Nitrogen heterocycles
Synthesis
Issue Date14-Jan-2004
PublisherElsevier
CitationTetrahedron Letters 45(7): 1559-1563 (2004)
AbstractThe fragmentation of primary alkoxyl radicals, often described as low yielding and plagued by side reactions, proceeded in good to excellent yields when aminol derivatives were used as substrates. Remarkably, no side reactions such as hydrogen abstraction or oxidation were observed. The fragmentation can be coupled with an alkylation reaction to give 2-substituted pyrrolidine and piperidine rings such as alkaloid analogues and functionalized, chiral nitrogen heterocycles.
Description5 pages, 1 table, 6 schemes.-- Printed version published Feb 9, 2004.
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2003.12.003
URIhttp://hdl.handle.net/10261/13459
DOI10.1016/j.tetlet.2003.12.003
ISSN0040-4039
Appears in Collections:(IPNA) Artículos

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