Alkenes from terminal epoxides using lithium 2, 2, 6, 6-tetramethylpiperidide and organolithiums or grignard reagents

DM Hodgson, MJ Fleming…

Index: Hodgson, David M.; Bray, Christopher D.; Kindon, Nicholas D. Journal of the American Chemical Society, 2004 , vol. 126, # 22 p. 6870 - 6871

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Citation Number: 32

Abstract

We recently reported the reaction of terminal epoxides with lithium 2,2,6,6-tetramethylpiperidide (LTMP), which proceeds through trapping of a trans-α-lithiated epoxide 2 5 with LTMP to give an enamine 3 (R 2 = tetramethylpiperidin-1-yl). 6 During this study we considered whether the presence of an organolithium might divert the chemistry to alkene synthesis. This could provide a solution to the limitations mentioned above, provided (i) α-lithiation of the epoxide by ...