English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/184944
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

Diastereoselective construction of the 6‑oxa-2- azabicyclo[3.2.1]octane scaffold from chiral α‑hydroxyaldehyde derivatives by the aza-prins reaction

AuthorsMahía Moros, Alejandro; Badorrey, Ramón ; Gálvez, José A. ; Díaz de Villegas, María D.
Issue Date2017
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 82(15): 8048-8057 (2018)
Abstract(R)-2,3-Di-O-benzylglyceraldehyde and N-tosyl homoallylamine undergo aza-Prins cyclization to afford (1R,5S,7S)-7-[(benzyloxy)methyl]-2-tosyl-6-oxa-2-azabicyclo[3.2.1]octane in a highly diastereoselective manner through an unexpected intramolecular nucleophilic attack. Our work has opened a new route toward the asymmetric synthesis of 7-(alkyl or aryl)-6-oxa-2-azabicyclo[3.2.1]octane derivatives from chiral α-hydroxyaldehyde derivatives in one step.
Publisher version (URL)https://doi.org/10.1021/acs.joc.7b01291
URIhttp://hdl.handle.net/10261/184944
DOI10.1021/acs.joc.7b01291
ISSN0022-3263
E-ISSN1520-6904
Appears in Collections:(ISQCH) Artículos
Files in This Item:
File Description SizeFormat 
accesoRestringido.pdf59,24 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.