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Xiao Han, Jacek Kwiatkowski, Feng Xue, Kuo-Wei Huang and Yixin Lu Asymmetric Mannich Reaction of Fluorinated Ketoesters with a Tryptophan-Derived Bifunctional Thiourea Catalyst Angewandte Chemie International Edition 48

Version of Record online: 8 SEP 2009 | DOI: 10.1002/anie.200903635

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Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β-lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).

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