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A Cascade Aza-Cope/Aza-Prins Cyclization Leading to Piperidine Derivatives

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Title A Cascade Aza-Cope/Aza-Prins Cyclization Leading to Piperidine Derivatives
 
Creator NALLASIVAM, JL
FERNANDES, RA
 
Subject CATALYTIC ASYMMETRIC AMINOALLYLATION
EFFICIENT SYNTHESIS
REARRANGEMENT
ALKALOIDS
ALDEHYDES
LIGANDS
ANALOGS
ACCESS
AMINES
ROUTE
Cascade reactions
Sigmatropic rearrangement
Cross-coupling
Nitrogen heterocycles
Cyclization
Lewis acids
 
Description The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines has been explored. The use of glyoxalic acid as the carbonyl component afforded bicyclic structures as a result of the internal carboxylate anion trapping the intermediate cation. The unimolecular bis-, tris-, and tetrakis(homoallylamine)s efficiently delivered the appended bis-, tris- and tetrakis(piperidine-4-ol)s (tripod and crucifix shape, respectively) as new entities. The latter compound served as an excellent ligand in the Suzuki-Miyaura cross-coupling reaction to synthesize incrustoporin.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2016-01-14T10:38:22Z
2016-01-14T10:38:22Z
2015
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(9)2012-2022
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201403607
http://dspace.library.iitb.ac.in/jspui/handle/100/17379
 
Language en