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Acid-Catalyzed Intramolecular [2+2] Cycloaddition of Ene-allenones: Facile Access to Bicyclo[n.2.0] Frameworks

Authors

  • Jun-Feng Zhao,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore), Fax: (+65) 6791-1961
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  • Teck-Peng Loh Prof. Dr.

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore), Fax: (+65) 6791-1961
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  • We gratefully acknowledge Nanyang Technological University and the Ministry of Education Academic Research Fund Tier 2 (grant nos. T206B1221 and T207B1220RS) for funding of this research.

Abstract

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Two plus two equals a bicycle: A highly efficient acid-catalyzed intramolecular [2+2] cycloaddition of ene-allenones affords strained bicyclo[n.2.0] frameworks, which contain vicinal all-carbon quaternary and tertiary centers (see scheme; Tf: trifluoromethanesulfonyl), under mild conditions with excellent yields and chemo-, regio-, and diastereoselectivities.

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