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Feierfeil J, Grossmann A, Magauer T. Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates. Angew Chem Int Ed Engl. 2015;54(40):11835-8doi: 10.1002/anie.201506232.
Feierfeil, J., Grossmann, A., & Magauer, T. (2015). Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates. Angewandte Chemie (International ed. in English), 54(40), 11835-8. https://doi.org/10.1002/anie.201506232
Feierfeil, Johannes, et al. "Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates." Angewandte Chemie (International ed. in English) vol. 54,40 (2015): 11835-8. doi: https://doi.org/10.1002/anie.201506232
Feierfeil J, Grossmann A, Magauer T. Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates. Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11835-8. doi: 10.1002/anie.201506232. Epub 2015 Aug 07. PMID: 26255867.
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Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11835-8. doi: 10.1002/anie.201506232. Epub 2015 Aug 07.

Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates.

Angewandte Chemie (International ed. in English)

Johannes Feierfeil, Adriana Grossmann, Thomas Magauer

Affiliations

  1. Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich.
  2. Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich. [email protected].

PMID: 26255867 DOI: 10.1002/anie.201506232

Abstract

Described is the development of a highly efficient 2π disrotatory ring-opening aromatization sequence using bicyclo[3.1.0]hexan-2-ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines or alcohols formation of substituted anilines or ethers, respectively, is achieved. Additionally, the utility of this method was demonstrated in a short synthesis of sekikaic acid methyl ester.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: X-ray diffraction; arenes; aromaticity; fused-ring systems; synthetic methods

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