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Synlett 1999; 1999(2): 213-215
DOI: 10.1055/s-1999-2577
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Diastereoselective Synthesis of Methylated α-Methoxy-8-oxabicyclo[3.2.1]oct-6-en-3-ones. Contrathermodynamic Introduction of Methoxy Group by Low Temperature [4 + 3]-Cycloaddition

S. Pierau* , H. M. R. Hoffmann
  • *Department of Organic Chemistry, University of Hannover, Schneiderberg 1 B, D-30167 Hannover, Germany; Fax +49(0)51 17 62 30 11; E-mail: hoffmann@mbox.oci.uni-hannover.de
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Publication Date:
31 December 1999 (online)

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A series of α,α-dimethoxysilyl enol ethers has been prepared and shown to undergo diastereoselective [4 + 3]-cycloaddition with furan and cyclopentadiene in the presence of catalytic trimethylsilyl triflate. The α-methoxy group of the resulting title oxabicyclics preferentially adopts the contrathermodynamic equatorial position.

α,α-dimethoxysilyl enol ethers - methoxy-2-silyloxyallyl cation intermediates - silicon bridging - kinetic control - dictyoxetane models

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