Diastereoselective access to trans-2-substituted cyclopentylamines.
A highly diastereoselective synthesis of trans-2-substituted cyclopentylamines via a tandem hydrozirconation/Lewis acid-mediated cyclization sequence applied to butenyl oxazolidines is described. The method allows an easy preparation of diversely substituted cyclopentylamines which appear to be useful synthetic intermediates. This was further illustrated by the syntheses of (±)-Rodocaine, (±)-trans-pentacin, and enantiomerically enriched trans-cyclopentane-1,2-diamine.
Joosten
Antoine
A
Institut de Chimie Moléculaire de Reims, CNRS (UMR 6229) and Université de Reims, 51687 Reims Cedex 2, France.
Lambert
Emilie
E
Vasse
Jean-Luc
JL
Szymoniak
Jan
J
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D000813:Anilides; D003517:Cyclopentanes; D058116:Lewis Acids; D010080:Oxazoles; C467768:cyclopentane-1,2-diamine; C064210:oxazolidine; C009190:rodocaine