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

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.

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