Practical method for. alpha.-alkenyl ketone synthesis based on a facile reductive rearrangement of alkynyl halohydrins

PA Wender, DA Holt, SM Sieburth

Index: Wender, Paul A.; Holt, Dennis A.; Sieburth, Scott M. Journal of the American Chemical Society, 1983 , vol. 105, # 10 p. 3348 - 3350

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Citation Number: 46

Abstract

76 I3: lJe a Cis: trans as determined by GC. undefined erythro: threo in acyclic alcohols as determined by GC. Reaction conducted at ambient temperature instead of-78" C. Yield determined by GC. e LiAIH,, NaOMe, THF, ambient temperature. fn-BuLi, DIBAL, THF, reflux. g Alkyne addition and reductive rearrangement carried out in a single operation. Only one isomer observed. 0.4 mole scale. J One mole scale. Bromocyclohexanone gave nearly ...