English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/52695
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:
Title

Experimental and theoretical studies on Mannich-type reactions of chiral non-racemicN-(benzyloxyethyl) nitrones

AuthorsDíez-Martínez, Alba; Tejero, Tomás ; Merino, Pedro
Issue Date2010
PublisherElsevier
CitationTetrahedron: Asymmetry 21(24): 2934-2943 (2010)
AbstractThe nucleophilic addition of both silyl ketene acetals and lithium enolates derived from methyl acetate to chiralnon-racemicN-(benzyloxyethyl)nitrones has been studied both experimentally and theoretically. Aromatic nitrones showed lower reactivity that aliphatic nitrones and the addition of the silyl ketene acetal led to lower selectivities than the addition of the corresponding lithium enolate. Whereas low selectivity was obtained for the addition of the silyl ketene acetal, only one diastereomer could be detected in all cases for the addition of lithium enolate to aliphatic nitrones. The synthetic utility of the two chiral auxiliaries employed lies in the preparation of enantiomeric compounds. DFT theoretical calculations confirmed the stepwise mechanism for the addition of silyl ketene acetals to nitrones and are in good agreement with the observed experimental results.
URIhttp://hdl.handle.net/10261/52695
DOI10.1016/j.tetasy.2010.12.004
Identifiersdoi: 10.1016/j.tetasy.2010.12.004
issn: 0957-4166
Appears in Collections:(ICMA) Artículos
Files in This Item:
File Description SizeFormat 
accesoRestringido.pdf15,38 kBAdobe PDFThumbnail
View/Open
Show full item record
Review this work
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.