Catalytic Asymmetric Synthesis of 4‑Nitropyrazolidines: An Access to Optically Active 1,2,3-Triamines

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 stereogen...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-08, Vol.136 (32), p.11296-11299
Main Authors: Lykke, Lennart, Carlsen, Bjørn Dreiø, Rambo, Raoní Scheibler, Jørgensen, Karl Anker
Format: Article
Language:English
Subjects:
Aldehydes
Alkenes - chemistry
Amines - chemistry
Catalysis
Crystallography, X-Ray
Hydrazones - chemistry
Hydrogen Bonding
Ketones - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Nitrogen - chemistry
Optics and Photonics
Oxygen - chemistry
Pyrazoles - chemistry
Solvents - chemistry
Stereoisomerism
Temperature
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja506694v