Enantioselective Synthesis of Imidazolines with Quaternary Stereocenters by Organocatalytic Reaction of N-(Heteroarenesulfonyl)imines with Isocyanoacetates
Enantioselective Synthesis of Imidazolines with Quaternary Stereocenters by Organocatalytic Reaction of N-(Heteroarenesulfonyl)imines with Isocyanoacetates
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DOI：
10.1021/ol301256q
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发表时间：
2012-06-15
期刊：
影响因子：
5.2
通讯作者：
Shibata, Norio
中科院分区：
文献类型：
--
作者：
Nakamura, Shuichi;Maeno, Yuri;Shibata, Norio
由奎宁衍生的手性硫脲催化的N-磺酰亚胺与异氰乙酸异氰酸酯的有机催化Mannich对映体反应生成了具有高非对映选择性和对映体选择性的2-咪唑啉类化合物(高达>；99：1 Dr.和96%的人)。该反应提供了一条方便的路线来获得各种咪唑啉和相关的具有高对映体纯度的季碳中心的α，β-二氨基酸。
An organocatalytic enantioselective Mannich-type reaction of isocyanoacetate with N-sulfonylimines catalyzed by chiral thioureas derived from quinine yielded 2-imidazolines with high diastereo- and enantioselectivities (up to >99:1 dr. and 96% ee). This reaction provided a convenient route to access various imidazolines and related alpha,beta-diamino acids having a quaternary carbon center in high enantiomeric purities.