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Synlett 1996; 1996(3): 283-284
DOI: 10.1055/s-1996-5373
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A Highly Stereoselective Synthesis of a Tetrahydrofluorene via a Domino Claisen Rearrangement Hetero-Ene Reaction

S. Lambrecht, H. J. Schäfer* , R. Fröhlich, M. Grehl
  • *Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Corrensstraße 40, D-48149 Münster, Germany
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Publication Date:
31 December 2000 (online)

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3-(Cyclohex-2-enyloxy)-4-methoxybenzaldehyde (2) is converted in high yield to rac-(4bR,8aS,9S)-tetrahydro-3-methoxy-5H-fluorene-4,9-diol (4) via a domino Claisen rearrangement hetero-ene reaction. With the corresponding acetal of aldehyde 2 the reaction ends after the Claisen rearrangement and 2-(cyclohex-2-enyl)-3-hydroxy-4-methoxybenzaldehyde is obtained after hydrolysis.

Claisen rearrangement - hetero-ene reaction - tetrahydrofluorene

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