Ethylation of 2-alkenyltetrahydrofurans and 2-alkenyltetrahydropyrans catalyzed by titaniun (IV) isoprpopoxide. Supplement to the synthesis of pheromones of lesser …

EA Matyushenkov, DG Churikov, NA Sokolov…

Index: Matyushenkov; Churikov; Sokolov; Kulinkovich Russian Journal of Organic Chemistry, 2003 , vol. 39, # 4 p. 478 - 485

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Citation Number: 8

Abstract

Abstract Reaction of 2-vinyltetrahydrofuran and 2-vinyltetrahydropyran with ethylmagnesium bromude in the presence ot titanium (IV) isopropoxide afforded in moderate selectivity trans- 4-octen-1-ol and trans-5-nonen-1-ol respectively. Best yields and high stereochemical purity of products were obtained in ethylation under these conditions of 2-(cis-1-propenyl) tetrahydrofuran, 2-(cis-1-proprnyl)-and 2-(trans-1-propenyl) tetrahydropyran. It is assumed ...