Cyclohydrocarbonylation-based strategy toward poly-substituted piperidines.
Org Lett
; 13(9): 2294-7, 2011 May 06.
Article
in En
| MEDLINE
| ID: mdl-21462951
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Piperidines
/
Hydrocarbons, Cyclic
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2011
Document type:
Article
Affiliation country:
Italy