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Addition of Borane to L-Chloro-1-En-3-Ynes. A New Synthesis of Alkyl (E)-β-Chloro-α, β-Unsaturated Ketones

硼烷對1-氯基-1-烯-3-炔類的加成反應烷基(反式)-β-氯基-α, β-不飽和酮的新合成方法

摘要


(反式)-1-氯基-1-烯-3-炔類化合物,可由氯化1-炔基鋅與1-碘基-2-氯基-1-烯類經由鈀催化之耦合反應而製得,其與硼烷作用,可將硼基選擇性地加入炔鍵中鄰烯之碳上,續在鹼性中氧化,可得中、高產率之烷基(反式)-β-氯基-α, β-不飽和酮類。

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並列摘要


(E)-1-Chloro-1-en-3-ynes 1, readily prepared by palladium-catalyzed cross coupling of 1-alkynylzinc chlorides with (E)-1-iodo-2-chloro-1-alkenes, reacted regioselectively with 1 equiv of borane at the triple bond followed by basic oxidation to yield acyclic alkyl (E)-β-chloro-α, β-unsaturated ketones 2 in moderate to good yields.

並列關鍵字

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