Enantioselective Nucleophilic Catalysis: The Synthesis of Aza-β-Lactams through [2+2] Cycloadditions of Ketenes with Azo Compounds

Enantioselective Nucleophilic Catalysis: The Synthesis of Aza-β-Lactams through [2+2] Cycloadditions of Ketenes with Azo Compounds

Get ready for take off: A planar‐chiral derivative of 4‐pyrrolidinopyridine (1) mediates the title transformation (see scheme) in a convergent manner with good enantioselectivity, thus giving the first catalytic asymmetric synthesis of aza‐β‐lactams.

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-09, Vol.47 (37), p.7048-7050
Hauptverfasser: Berlin, Jacob M, Fu, Gregory C
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
azo compounds
Azo Compounds - chemistry
beta-Lactams - chemical synthesis
Catalysis
Ethylenes - chemistry
heterocycles
homogeneous catalysis
Ketones - chemistry
lactams
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Zusammenfassung:Get ready for take off: A planar‐chiral derivative of 4‐pyrrolidinopyridine (1) mediates the title transformation (see scheme) in a convergent manner with good enantioselectivity, thus giving the first catalytic asymmetric synthesis of aza‐β‐lactams.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802439