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


  • We thank Dr. Xing Dai, Dr. Maximilian Dochnahl, and Takashi Nakai for helpful discussions and for experimental assistance. Support was provided by the NIH (National Institute of General Medical Sciences: grant no. R01-GM57034), Merck Research Laboratories, and Novartis.


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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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