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Synlett 1999; 1999(6): 705-708
DOI: 10.1055/s-1999-2737
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Formation of Four- to Six-Membered Carbocycles by Tandem Brook Rearrangement-Intramolecular Michael Reaction

Kei Takeda* , Tadashi Tanaka
  • *Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0194, Japan; Fax +81-7 64-34-50 49; E-mail: takedak@ms.toyama-mpu.ac.jp
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Publication Date:
31 December 1999 (online)

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A tandem Brook rearrangement-intramolecular Michael reaction has been developed as a synthetic route to functionalized carbocycles. Acylsilanes, tethered by a two-, three-, or four-carbon chain to an acrylate Michael acceptor, have been prepared and used as the cyclization substrates. Treatment of these compounds with PhLi or LiP(O)(OMe)2 at temperatures below 0 °C results in the formation of four- to six-membered carbocycles in good yields.

tandem reaction - acylsilane - Brook rearrangement - intramolecular Michael reaction - carbocycles

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