Synthesis of Azepine Derivatives by Rhodium-Catalyzed Tandem 2,3-Rearrangement/Heterocyclization†
Corresponding Author
Prof. Dr. Itaru Nakamura
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980-8578 (Japan) http://www.orgreact.sakura.ne.jp/en-index.html
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980-8578 (Japan) http://www.orgreact.sakura.ne.jp/en-index.htmlSearch for more papers by this authorMasashi Okamoto
Department of Chemistry, Graduate School of Science, Tohoku University (Japan)
Search for more papers by this authorYoshinori Sato
Department of Chemistry, Graduate School of Science, Tohoku University (Japan)
Search for more papers by this authorProf. Dr. Masahiro Terada
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980-8578 (Japan) http://www.orgreact.sakura.ne.jp/en-index.html
Search for more papers by this authorCorresponding Author
Prof. Dr. Itaru Nakamura
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980-8578 (Japan) http://www.orgreact.sakura.ne.jp/en-index.html
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980-8578 (Japan) http://www.orgreact.sakura.ne.jp/en-index.htmlSearch for more papers by this authorMasashi Okamoto
Department of Chemistry, Graduate School of Science, Tohoku University (Japan)
Search for more papers by this authorYoshinori Sato
Department of Chemistry, Graduate School of Science, Tohoku University (Japan)
Search for more papers by this authorProf. Dr. Masahiro Terada
Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai, 980-8578 (Japan) http://www.orgreact.sakura.ne.jp/en-index.html
Search for more papers by this authorThis work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Molecular Activation Directed toward Straightforward Synthesis” from the Ministry of Education, Culture, Sports, Science and Technology (Japan).
Graphical Abstract
Easy to N-cycle: The efficient synthesis of azepine derivatives was achieved by Rh-catalyzed tandem 2,3-rearrangement involving the heterocyclization of N-allenylnitrone intermediates (see scheme; cod=1,5-cyclooctadiene, tppms=sodium diphenylphosphinobenzene-3-sulfonate).
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
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