Aminal–Pyrrolidine Organocatalysts – Highly Efficient and Modular Catalysts for α‐Functionalization of Carbonyl Compounds
Aminal–Pyrrolidine Organocatalysts – Highly Efficient and Modular Catalysts for α‐Functionalization of Carbonyl Compounds
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DOI：
10.1002/ejoc.200901283
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发表时间：
2010-02
影响因子：
2.8
通讯作者：
Adrien Quintard;Sébastien Belot;Estelle Marchal;A. Alexakis*
中科院分区：
文献类型：
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作者：
Adrien Quintard;Sébastien Belot;Estelle Marchal;A. Alexakis*
羟脯氨酸的4位被苯酚取代，与2位上的氨基一起，产生了协同效应，形成了两个强大的互补有机催化剂。它们在一系列直链/支链醛和酮的-官能化反应中表现出极好的对映体控制性，包括与乙二基二磺酸的Michael加成反应或对硝基苯乙烯的-胺化反应。以较低的催化剂负载量(降至1%摩尔分数)，可获得高达98.5%的反应效率。作为效率的证明，可以获得高达1000h-1的TOF。
The substitution of the 4-position of hydroxyproline by aphenol group, together with an aminal on the 2-position, gave a synergistic effect leading to two powerful complementary organocatalysts. They show excellent enantiocontrol in the -functionalization of a wide range of linear/branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and -amination. We obtained ees up to 98.5 % with low catalyst loadings (down to 1 mol-%). As a proof of efficiency, TOFs of up to 1000 h-1 could be obtained.