Practical Asymmetric Synthesis of 1,2-Diamines in the 3-Aminoazepane Series
Authors:
- 20 February 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (7) , 2645-2651
Abstract
A simple and versatile method for the enantio- and diastereoselective synthesis of mono- or disubstituted 3-aminoazepanes is described. The key step involves a highly regio- and diastereoselective tandem ring-enlargement/alkylation or reduction process. This novel synthetic route provides enantiomerically pure constrained diamines interesting as scaffolds for medicinal chemistry.Keywords
This publication has 18 references indexed in Scilit:
- Expansion to Seven-Membered RingsTetrahedron, 2000
- AMINESviaNUCLEOPHJLIC 1,2-ADDITION TO KETIMINES. CONSTRUCTION OF NITROGEN-SUBSTITUTED QUATERNARY CARBON ATOMS. A REVIEWOrganic Preparations and Procedures International, 2000
- Diastereoselective synthesis of 2-aryl-3-aminoazepanes via a novel ring-enlargement processTetrahedron Letters, 2000
- A novel series of N-(hexahydr-1,4-diazepin-6-yl) and N-(hexahydroazepin-3-yl)benzamides with high affinity for 5-HT3 and dopamine D2 receptorsBioorganic & Medicinal Chemistry Letters, 1998
- Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bondTetrahedron: Asymmetry, 1997
- Development of Novel, Potent, and Selective Dopamine Reuptake Inhibitors through Alteration of the Piperazine Ring of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909)Journal of Medicinal Chemistry, 1996
- A STABLE CHIRAL 1,4-DIHYDROPYRIDINE EQUIVALENT FOR THE ASYMMETRIC SYNTHESIS OF SUBSTITUTED PIPERIDINES: 2-CYANO-6-PHENYLOXAZOLOPIPERIDINEOrganic Syntheses, 1992
- Practical enantioselective Diels-Alder and aldol reactions using a new chiral controller systemJournal of the American Chemical Society, 1989
- Synthesis and cation-extraction study of lithium-selective chromogenic 14-crown-4 derivativesThe Journal of Organic Chemistry, 1987
- Nucleophilic additions to tetrahydropyridinium salts. Applications to alkaloid synthesesAccounts of Chemical Research, 1984