A Simple Enantioconvergent and Chemoenzymatic Synthesis of Optically Active α-Substituted Amides†
Dr. Wiktor Szymański
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorAlja Westerbeek
Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Dr. Dick B. Janssen
Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Dick B. Janssen, Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Ben L. Feringa, Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Dr. Ben L. Feringa
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Dick B. Janssen, Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Ben L. Feringa, Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorDr. Wiktor Szymański
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorAlja Westerbeek
Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Dr. Dick B. Janssen
Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Dick B. Janssen, Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Ben L. Feringa, Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Dr. Ben L. Feringa
Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Dick B. Janssen, Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Ben L. Feringa, Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
Search for more papers by this authorWe thank Theodora Tiemersma-Wegman and Monique Smith for their technical assistance with HPLC and GC analyses.
Graphical Abstract
Einfach und effizient: Die Kombination einer enzymatischen, enantioinvertierenden Reaktion mit einfachen Folgeprozessen ermöglicht die Umwandlung racemischer Verbindungen in chirale α-substituierte Amide (siehe Bild; Ms=Methansulfonyl). Diese wichtigen Bausteine werden in hoher Gesamtausbeute und mit hohem Enantiomerenüberschuss erhalten; die entfallende Aufreinigung der Intermediate führt zu einem zeit- und kosteneffizienten Prozess.
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