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Hexafluoroacetone as a protecting and activating reagent: 5,5-difluoro- and trans-5-fluoropipecolic acids from glutamic acid
Authors:Alexander S. Golubev  Hartmut Schedel  Marco Fioroni  Sven Thust
Affiliation:a Department of Organic Chemistry, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany
b Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, GSP-1, V-334 Rus-117813 Moscow, Russia
c Department of Chemistry, Technical University of Eindhoven, Helix Building, Eindhoven, The Netherlands
Abstract:
Starting from hexafluoroacetone-protected (S)-glutamic acid, trans-5-fluoropipecolic and 5,5-difluoropipecolic acid have been synthesized. The piperidine ring was constructed by an intramolecular metal carbenoid NH insertion.
Keywords:Glutamic acid   Hexafluoroacetone   Diazo ketones   Metal carbenoid NH insertion   DAST fluorination
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