Intramolecular Alkynylcyclopropanation of Olefins Catalyzed by Bi(OTf)3: Stereoselective Synthesis of 1-Alkynyl-3-azabicyclo[3.1.0]hexanes

Authors

  • Kimihiro Komeyama Dr.,

    1. Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
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  • Natsuko Saigo,

    1. Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
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  • Motoyoshi Miyagi,

    1. Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
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  • Ken Takaki Prof. Dr.

    1. Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan), Fax: (+81) 82-424-5494
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  • We 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.

Abstract

original image

Zwei Ringe auf einen Schlag: 1-Alkinyl-3-azabicyclo[3.1.0]hexane 2 entstanden in guten bis ausgezeichneten Ausbeuten bei der stereoselektiven Bi(OTf)3-katalysierten dehydratisierenden Alkinylcyclopropanierung der Azaeninole 1, wobei das Propargylalkoholmotiv von 1 als Propargylcarben-Syntheseäquivalent fungierte.

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