Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/5949
Title: Cyclohydrocarbonylation-based strategy toward poly- susbtituted piperidines
Authors: Arena, Giada
Zill, N
Salvadori, Jessica
Girard, N
Mann, A
Taddei, Maurizio 
Issue Date: 2011
Project: None 
Journal: ORGANIC LETTERS
Abstract: 
Convenient accesses to enantiomerically pure 2-, 2,3-, 2,6-, 2,3,6-substituted piperidines and 1,4-substituted indolizine are described. At first, indium-mediated aminoallylation and -crotylation of aldehydes with (R)-phenylglycinol or (1R,2S)-1-amino-2-indanol gave homoallylamines with high stereocontrol. Then, these products, submitted to a Rh(I)-catalyzed hydroformylative cyclohydrocarbonylation, afforded perhydrooxazolo [3,2-a]piridines whose oxazolidines are opened with nucleophiles. Finally, the removal of the chiral auxiliaries delivered the enantiomerically pure piperidines.
Description: 
21423
URI: http://hdl.handle.net/20.500.12779/5949
ISSN: 1523-7060
DOI: 10.1021/ol200557r
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