Title :

The Reactivity of Enantiopure ( S )‐6‐Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions

Author(s) :

Šafář, Peter [Auteur]
Slovak University of Technology in Bratislava [STU]
Marchalín, Štefan [Auteur]
Slovak University of Technology in Bratislava [STU]
Balónová, Barbora [Auteur]
University of Kent [Canterbury]
Šoral, Michal [Auteur]
Slovak University of Technology in Bratislava [STU]
Moncol, Ján [Auteur]
Slovak University of Technology in Bratislava [STU]
Ghinet, Alina [Auteur]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Rigo, Benoît [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Daïch, Adam [Auteur]
Unité de Recherche en Chimie Organique et Macromoléculaire [URCOM]

Journal title :

European Journal of Organic Chemistry

Pages :

5499-5511

Publisher :

Wiley-VCH Verlag

Publication date :

2018-10-18

ISSN :

1434-193X

HAL domain(s) :

Chimie

English abstract : [en]

Enantiopure N ‐benzyl 6‐oxopipecolic acid, obtained from ( S )‐2‐aminoadipic acid, was evaluated under π‐cationic cyclization conditions. If the combination of SOCl 2 /AlCl 3 seems to be superior in terms of the reaction ...
Show more >Enantiopure N ‐benzyl 6‐oxopipecolic acid, obtained from ( S )‐2‐aminoadipic acid, was evaluated under π‐cationic cyclization conditions. If the combination of SOCl 2 /AlCl 3 seems to be superior in terms of the reaction yields, use of PPA, (CF 3 CO) 2 O/BF 3 · Et 2 O, and Eaton's reagent is also very interesting since in addition to the expected keto‐lactam, reduced‐ and oxidized keto‐lactam, enamides and enamidones containing CF 3 CO– residue are isolated. Mechanisms leading to these products as well as the ones resulting from their acidic treatment were proposed and discussed with the help, in some cases, of univocal transformations and X‐ray analysis.Show less >

Language :

Anglais

Popular science :

Non

Collections :

• Facteurs de risque et déterminants moléculaires des maladies liées au vieillissement (RID-AGE) - U1167

Source :

Harvested from HAL