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Synlett 1995; 1995(10): 1071-1072
DOI: 10.1055/s-1995-5188
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Preparation of α-Bromoenolates from α,α-Dibromoketones with n-BuLi, PhMgBr, or Et2Zn via Halogen-Metal Exchange Reaction

Yoshitaka Aoki, Koichiro Oshima* , Kiitiro Utimoto1
  • *Division of Material Chemistry, Faculty of Engineering, Kyoto University, Sakyo-ku, Kyoto, 606-01, Japan
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Publication Date:
31 December 2000 (online)

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Treatment of α,α-dibromoketones with n-BuLi, PhMgBr, or Et2Zn gave the corresponding α-bromoenolates via halogen-metal exchange reaction. The resulting α-bromoenolates reacted wit aldehydes to provide α,β-epoxy ketones, bromohydrins, or α,β-unsaturated ketones, respectively.

α-bromoenolate - α,α-dibromoketone - halogen-metal exchange