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Communication | Regular issue | Vol 48, No. 7, 1998, pp.1325-1330
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8161
Stereocontrolled Synthesis of Tetrahydrofurans and Tetrahydropyrans by Cyclisation of Hydroxyselenides

Luca Arista, Michelangelo Gruttadauria,* and Renato Noto

*Dipartimento di Chimica Organica, Universita di Palermo, Via Archirafi 20 90123 Palermo, Italy


An efficient stereocontrolled synthesis of 2,3,5-trisubstituted tetrahydrofuran and 2,4,6-trisubstituted tetrahydropyran rings from homoallylic alcohols (16) and (18) was achieved by: i) epoxidation; ii) ring opening of the epoxide with sodium phenyl selenide; iii) cleavage of the TBDMS group with a stereoconvergent elimination of water followed by intramolecular oxygen nucleophile capture. The presence of a branching near to the selenonium ring made the attack in the exo mode faster than the attack in the endo/exo mode.