Tetrahedron

Alkylation reactions of anions derived from 2-benzenesulphonyl tetrahydropyran and their application to spiroketal syntiesis

SV Ley, B Lygo, F Sternfeld, A Wonnacott

Index: Ley, Steven V.; Lygo, Barry; Sternfeld, Francine; Wonnacott, Anne Tetrahedron, 1986 , vol. 42, # 15 p. 4333 - 4342

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Citation Number: 90

Abstract

Reaction of 3, 4-dihydro-2H-pyran or 2-methoxytetrahydropyran with benzenesulphinic acid gave 2-benzenesulphonyl tetrahydropyran (1)., Deprotonation of (1) follwed by alkylation with carbonyl compounds or halides gave cyclic enol ether addition products by spontaneous elimination of benzenesulphinic acid. Interception of the initial addition products with aldehydes by reductive desulphonylation to give alkylated tetrahydropyran ...