Construction of highly functionalized diazoacetoacetates via catalytic Mukaiyama-Michael reactions
Construction of highly functionalized diazoacetoacetates via catalytic Mukaiyama-Michael reactions
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DOI：
10.1021/ol800298n
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发表时间：
2008-04-17
期刊：
影响因子：
5.2
通讯作者：
Doyle, Michael P.
中科院分区：
文献类型：
--
作者：
Liu, Yu;Zhang, Yu;Doyle, Michael P.
功能化重氮乙酰乙酸酯是通过 3-(三烷基硅烷氧基)-2-重氮基-3-丁烯酸甲酯和 α,β-不饱和烯酮之间的有效 Mukaiyama-Michael 反应制备的。通过这种方法，乙烯基醚和酮衍生物都可以以良好到优异的产率获得。温和的路易斯酸三氟甲磺酸锌(II)是最佳催化剂，其负载量可低至0.1 mol%。此外，三氟甲磺酸锌也被发现是相关向山醇醛反应的优良催化剂。
Functionalized diazo acelloacetates are prepared by an efficient Mukaiyama-Michael reaction between methyl 3-(trialkylsilanoxy)-2-diazo-3-butenoate and alpha,beta-unsaturated enones. Vinyl ether and ketone derivatives are both accessible in good to excellent yield through this methodology. The mild Lewis acid zinc(II) triflate is the optimal catalyst, and its loading can be as low as 0.1 mol %. In addition, zinc triflate was also found to be a superior catalyst for the related Mukaiyama-aldol reaction.