MgI2-catalyzed halo aldol reaction: a practical approach to (E)-beta-iodovinyl-beta'-hydroxyketones.
MgI2-catalyzed halo aldol reaction: a practical approach to (E)-beta-iodovinyl-beta'-hydroxyketones.
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MgI2 催化的卤代羟醛反应：制备 (E)-β-碘乙烯基-β-羟基酮的实用方法。
DOI：
10.1039/b409056j
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发表时间：
2004
影响因子：
3.2
通讯作者：
Li,Guigen
中科院分区：
文献类型：
--
作者：
Wei,Han-Xun;Timmons,Cody;Farag,MohamedAli;Pare,PaulW;Li,Guigen
以三甲基碘硅烷（TMS-I）为原料，在二氯甲烷中于0 °C无催化剂条件下与α，β-不饱和酮反应，合成了新一代1-碘-3-硅氧基-1，3-丁二烯。以碘化镁为催化剂，这些丁二烯中间体与醛的卤代羟醛缩合反应得以有效进行。在新条件下合成了12个β-碘-α，β-不饱和-β′-羟基酮（卤代醛醇），具有良好的几何选择性和化学产率（11个实例的化学产率>80%）。
A novel generation of 1-iodo-3-siloxy-1,3-butadienes has been developed by reacting trimethylsilyl iodide (TMS-I) with α,β-unsaturated ketones in dichloromethane at 0 °C without the use of any catalyst. The halo aldol reaction of these butadiene intermediates with aldehydes was efficiently carried out by using magnesium iodide as the catalyst. Twelve β-iodo-α,β-unsaturated-β′-hydroxyketones (halo aldols) have been synthesized under the new condition with excellent geometric selectivity and good chemical yields (>80% chemical yields for 11 examples).