Selective isomerization of 1, 2-epoxyalkanes to aldehydes with lithium dialkylamides

A Yanagisawa, K Yasue, H Yamamoto

Index: Yanagisawa, Akira; Yasue, Katsutaka; Yamamoto, Hisashi Journal of the Chemical Society, Chemical Communications, 1994 , # 18 p. 2103 - 2104

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Citation Number: 27

Abstract

Reaction of a variety of 1, 2-epoxyalkanes with 2.5 equiv. of bulky metal amide—lithium 2, 2, 6, 6-tetramethylpiperidide—affords the corresponding aldehydes exclusively in high yields; this is the first example of base-promoted isomerization of monosubstituted epoxides to aldehydes.