title: Catalytic asymmetric synthesis of 4-nitropyrazolidines: an access to optically active 1,2,3-triamines.
abstract: The first catalytic enantio- and diastereoselective synthesis of 4-nitropyrazolidines is presented. Asymmetric hydrogen-bonding activation of nitro-olefins facilitated the 1,3-dipolar cycloaddition with hydrazones, affording optically active 4-nitropyrazolidines containing three continuous stereogenic centers as a single diastereomer in up to 99% ee. Furthermore, it is demonstrated that the optically active 4-nitropyrazolidines can be applied as precursors for the synthesis of highly interesting 1,2,3-triamines.
authors: Center for Catalysis, Department of Chemistry, Aarhus University , DK-8000 Aarhus C, Denmark.
authors: Lennart
authors: L
authors: Lykke
authors: Bjørn Dreiø
authors: BD
authors: Carlsen
authors: Raoní Scheibler
authors: RS
authors: Rambo
authors: Karl Anker
authors: KA
authors: Jørgensen
mesh_terms: D000447:Aldehydes; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006835:Hydrazones / Q000737:chemistry; D006860:Hydrogen Bonding; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D055095:Optics and Photonics; D010100:Oxygen / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000588:Amines; D006835:Hydrazones; D007659:Ketones; D011720:Pyrazoles; D012997:Solvents; D009584:Nitrogen; D010100:Oxygen