Straightforward Synthesis of Succinimide-Fused Pyrrolizidines by A Three-Component Reaction of α-Diketone, Amino Acid, and Maleimide
Straightforward Synthesis of Succinimide-Fused Pyrrolizidines by A Three-Component Reaction of α-Diketone, Amino Acid, and Maleimide
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DOI：
10.1055/s-0040-1706608
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发表时间：
2020-12-03
影响因子：
2.6
通讯作者：
Zhao, Yufen
中科院分区：
文献类型：
--
作者：
Shen, Peng;Guo, Yeting;Zhao, Yufen
研究了由α-二羰基化合物（环状和非环状二酮或酮酯）和氨基酸得到的甲亚胺叶立德与马来酰亚胺在无催化剂条件下的一锅三组分[3+2]环加成反应。该级联方案显示出高效率和显著的官能团耐受性，并且以高产率和优异的非对映选择性获得了具有高度紧凑和应变支架的普遍存在的琥珀酰亚胺稠合的吡咯烷。此外，这种新颖的和原子经济的策略可以在克规模上进行，具有相当的反应效率。
An efficient, one-pot, three-component [3+2] cycloaddition reaction of azomethine ylide obtained from alpha-dicarbonyl compounds (cyclic and acyclic diketone or keto ester) and amino acids with maleimides under catalyst-free conditions has been developed. This cascade protocol shows high efficiency and remarkable functional group tolerance, and the ubiquitous succinimide-fused pyrrolizidines with a highly compact and strained scaffold were obtained with high yield and excellent diastereoselectivity. Furthermore, this novel and atom-economical strategy could be performed on a gram scale with comparable reaction efficiency.