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Intramolecular [2+2] Cycloadditons of Ketenes and Olefins

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Strain and Its Implications in Organic Chemistry

Part of the book series: NATO ASI Series ((ASIC,volume 273))

Abstract

The synthetic potential of the intramolecular ketene cycloaddition is presented. It proves to be a versatile method for the synthesis of a variety of bi- and tricyclic cyclobutanones. The major side reaction, namely the dimerization of the ketene is prevented by the introduction of conformational restrictions. This has been achieved by an additional double bond or by an annulated ring system. Following this strategy C-analogues of a penem and a carbapenem as well as linear and angular annulated triquinanes are obtained in high yield.

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Authors and Affiliations

  1. Central Research Laboratories, CIBA-GEIGY Ltd., CH-4002, Basel, Switzerland

    Beat Ernst, Alain de Mesmaeker, Hans Greuter & Siem J. Veenstra

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  1. Beat Ernst
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  2. Alain de Mesmaeker
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  4. Siem J. Veenstra
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Editors and Affiliations

  1. Institut für Organische Chemie, Universität Hamburg, Hamburg, Germany

    Armin de Meijere

  2. Institut für Organische Chemie, Universität Bonn, Bonn, Germany

    Siegfried Blechert

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© 1989 Kluwer Academic Publishers

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Ernst, B., de Mesmaeker, A., Greuter, H., Veenstra, S.J. (1989). Intramolecular [2+2] Cycloadditons of Ketenes and Olefins. In: de Meijere, A., Blechert, S. (eds) Strain and Its Implications in Organic Chemistry. NATO ASI Series, vol 273. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0929-8_14

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  • DOI: https://doi.org/10.1007/978-94-009-0929-8_14

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