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Synlett 1990; 1990(1): 40-42
DOI: 10.1055/s-1990-20979
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A Highly Diastereoselective Route to Disubstituted Tetrahydrofuran Derivatives by Substitution of γ-Lactols with Silylated Nucleophiles

Andreas Schmitt* , Hans-Ulrich Reissig
  • *Institut für Organische Chemie der Technischen Hochschule Darmstadt, Petersenstraße 22, D-6100 Darmstadt, Federal Republic of Germany
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Publikationsdatum:
08. März 2002 (online)

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Easily available γ-lactols (2-hydroxytetrahydrofurans) 3, 5, and 7 are converted into 2,3-, 2,4-, and 2,5-disubstituted tetrahydrofurans 4, 6, and 8, respectively, by ether-boron trifluoride promoted substitution employing allylsilanes, propargylsilane, or a silyl enol ether as nucleophiles. The highest trans-selectivities are obtained for 2,4-disubstituted derivatives 6. The results are interpreted with the Felkin-Anh model, which nicely explains the high 1,3-induction observed.