Stereoselective Synthesis of (2Z)-2,4-Dienamides via NBS-Mediated Allyloxyl Addition-Claisen Rearrangement-Dehydrobromination Cascade Reaction of Ynsulfonamides
Stereoselective Synthesis of (2Z)-2,4-Dienamides via NBS-Mediated Allyloxyl Addition-Claisen Rearrangement-Dehydrobromination Cascade Reaction of Ynsulfonamides
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NBS介导的Yn磺酰胺烯丙氧基加成-Claisen重排-脱溴化氢级联反应立体选择性合成(2Z)-2,4-二烯酰胺
DOI：
10.1021/acs.orglett.5b01859
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发表时间：
2015-08-21
期刊：
影响因子：
5.2
通讯作者：
Zhai, Hongbin
中科院分区：
文献类型：
--
作者：
Ding, Runbo;Li, Yun;Zhai, Hongbin
本文报道了一个由NBS促进的烯丙氧基加成-Claisen重排-脱氨缩合级联反应。20多种取代炔基磺酰胺与烯丙醇反应，以中高产率合成了（2 Z）-2，4-二酰胺。已经提出了一个机械模型来解释包括立体化学结果的整个反应序列。理论计算表明[3，3] σ转移重排是限速步骤。
An NBS-promoted allyloxyl addition-Claisen reatrangement-dehydrobtomination cascade reaction has been developed. More than 20 substituted alkynylsulfonamides were reacted with allyl alcohols to generate (2Z)-2,4-dienamides in moderate to high yields. A mechanistic model has been proposed to account for the overall reaction sequence including the stereochemical outcome. Theoretical calculations suggested that a [3,3] sigmatropic rearrangement be the rate-limiting step.