Tandem Ring Opening/Cyclization of Vinylcyclopropanes: A Facile Synthesis of Chiral Bicyclic Amidines

Authors

  • Venkataraman Ganesh,

    1. Department of Organic Chemistry, Indian Institute of Science, Bangalore-560 012, Karnataka (India), Fax: (+91) 80-2360-2423
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    • These authors contributed equally.

  • Dr. Devarajulu Sureshkumar,

    1. Department of Organic Chemistry, Indian Institute of Science, Bangalore-560 012, Karnataka (India), Fax: (+91) 80-2360-2423
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    • These authors contributed equally.

  • Prof. Srinivasan Chandrasekaran

    Corresponding author
    1. Department of Organic Chemistry, Indian Institute of Science, Bangalore-560 012, Karnataka (India), Fax: (+91) 80-2360-2423
    • Department of Organic Chemistry, Indian Institute of Science, Bangalore-560 012, Karnataka (India), Fax: (+91) 80-2360-2423
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  • We thank the CSIR (New Delhi) for the Shyama Prasad Mukherjee Fellowship (V.G.) and DST for the JC Bose National Fellowship (S.C.).

Abstract

original image

Ring auf, Ring zu: Eine bromkatalysierte Tandemsequenz aus Ringöffnung und Cyclisierung von bicyclischen Vinylcyclopropanen mit Chloramin-T ([TsNCl]Na) liefert chirale bicyclische Amidinderivate in guten Ausbeuten. Auf Grundlage der experimentellen Beobachtungen wird ein plausibler Mechanismus vorgeschlagen. Ts=p-Toluolsulfonyl.

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