Enantioselective synthesis of spirocyclic aminochroman derivatives according to the CN(R,S) strategy.
Enantiomerically pure (3'R)- and (3'S)-3',4'-dihydrospiro[piperidine-2,3'(2'H)-benzopyran]s (R)-10 and (S)-10 were successfully synthesized according to the CN(R,S) methodology with the aim of serving as a pattern for the generation of related spirocyclic compounds. Two different synthetic pathways were studied starting from 2-cyano-6-phenyloxazolopiperidine (-)-2. One of them was selected and used for the preparation of amines (R)-17 and (S)-17 starting from (-)-2 and (+)-2, respectively. The enantiomeric purity of all final aminochroman derivatives was determinated by capillary electrophoresis using beta-cyclodextrin as the chiral selector.
Pavé
Grégoire
G
Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d'Orléans, BP 6759, 45067 Orléans Cedex 2, France.
Léger
Jean-Michel
JM
Jarry
Christian
C
Viaud-Massuard
Marie-Claude
MC
Guillaumet
Gérald
G
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003505:Cyclodextrins / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D002839:Chromans; D003505:Cyclodextrins; D007202:Indicators and Reagents