A mild procedure for the Lewis acid-catalyzed ring-opening of activated cyclopropanes with amine nucleophiles.
The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptake inhibitor (3R)-3-(1 H-indol-1-yl)- N-methyl-3-phenylpropan-1-amine.
Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7.
Olga
O
Lifchits
André B
AB
Charette
D000143:Acids / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009638:Norepinephrine / Q000037:antagonists & inhibitors; D012702:Serotonin Antagonists / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D000143:Acids; D000588:Amines; D003521:Cyclopropanes; D012702:Serotonin Antagonists; C030797:cyclopropane; D009638:Norepinephrine