Intramolecular Alkynylcyclopropanation of Olefins Catalyzed by Bi(OTf)3: Stereoselective Synthesis of 1-Alkynyl-3-azabicyclo[3.1.0]hexanes†
Kimihiro Komeyama Dr.
Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
Search for more papers by this authorNatsuko Saigo
Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
Search for more papers by this authorMotoyoshi Miyagi
Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
Search for more papers by this authorKen Takaki Prof. Dr.
Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
Search for more papers by this authorKimihiro Komeyama Dr.
Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
Search for more papers by this authorNatsuko Saigo
Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
Search for more papers by this authorMotoyoshi Miyagi
Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
Search for more papers by this authorKen Takaki Prof. Dr.
Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
Search for more papers by this authorWe thank H. Fukuoka for X-ray analysis. This work was partially supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT). K.K. acknowledges financial support from the Electric Technology Research Foundation of Chugoku.
Graphical Abstract
The postman always rings twice: 1-Alkynyl-3-azabicyclo[3.1.0]hexanes 2 were obtained in good to excellent yields from the stereoselective Bi(OTf)3-catalyzed dehydrative alkynylcyclopropanation of azaenynols 1, in which the propargyl alcohol motif of 1 acted as a propargyl carbene synthetic equivalent.
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