A Highly Diastereoselective Route to Disubstituted Tetrahydrofuran Derivatives  by Substitution of γ-Lactols with Silylated Nucleophiles

Andreas Schmitt; Hans-Ulrich Reissig

doi:10.1055/s-1990-20979

Synlett 1990; 1990(1): 40-42
DOI: 10.1055/s-1990-20979

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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.

PDF (161 kb)