Alkylation reactions of anions derived from 2-benzenesulphonyl tetrahydropyran and their application to spiroketal syntiesis
作者： Steven V. Ley , Barry Lygo , Francine Sternfeld , Anne Wonnacott
DOI: 10.1016/S0040-4020(01)87660-2
关键词: Tetrahydropyran 、 Yield (chemistry) 、 Sodium naphthalenide 、 Organic anion 、 Chemistry 、 Organic chemistry 、 Acetal 、 Deprotonation 、 Alkylation 、 Enol ether
摘要: Abstract Reaction of 3,4-dihydro-2H-pyran or 2-methoxytetrahydropyran with benzenesulphinic acid gave 2-benzenesulphonyl tetrahydropyran (1)., Deprotonation (1) follwed by alkylation carbonyl compounds halides cyclic enol ether addition products spontaneous elimination acid. Interception the initial aldehydes reductive desulphonylation to give alkylated derivatives proeeeded in moderate yield using sodium naphthalenide. Several cystic were further converted spiroketals including syntheses natural product pheromones from Dacus oleae and Paravespula vulgaris .
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