Intramolecular C(sp3)N Coupling by Oxidation of Benzylic C,N-Dianions†
Jenna L. Jeffrey
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
Search for more papers by this authorEmily S. Bartlett
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
Search for more papers by this authorCorresponding Author
Prof. Richmond Sarpong
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)===Search for more papers by this authorJenna L. Jeffrey
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
Search for more papers by this authorEmily S. Bartlett
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
Search for more papers by this authorCorresponding Author
Prof. Richmond Sarpong
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)===Search for more papers by this authorWe thank Dr. Vishnumaya Bisai (IISER Bhopal), Dr. André Isaacs (College of the Holy Cross (USA)), and Erica D’Amato (visiting undergraduate Amgen Scholar, 2011) for assistance with the preparation of starting materials for an initial study. This work was supported by the NIH-USA (NIGMS RO1 GM86374) and a Research Scholar Grant from the American Cancer Society-USA (RSG-09-017-01-CDD to R.S.). R.S. is a Camille Dreyfus Teacher Scholar. J.L.J. is grateful to the NSF for a graduate fellowship. E.S.B was supported by a Chemical Biology Interface Training Grant from the NIH (T32 GM066698). We are grateful to Eli Lilly, Abbott, and Roche for unrestricted financial support.
Graphical Abstract
Clever verknüpft! Eine intramolekulare C(sp3)-N-Kupplung zur Bildung von Azacyclen wird beschrieben. Die Reaktion verläuft über die Oxidation von benzylischen C,N-Dianionen mit Iod und knüpft an eine frühere Entdeckung bei der Synthese von Lyconadin A an. Die vorliegende Studie nutzt konformativ freie Substrate mit weniger aciden C-H-Bindungen und weniger reaktiven Stickstoffnukleophilen. ZnCl2 wurde als ein wichtiges Additiv identifiziert.
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