The Design and Synthesis of Phenylcyclopropane-Based Secondary Amine Catalysts and Their Applications in Asymmetric Reactions
The Design and Synthesis of Phenylcyclopropane-Based Secondary Amine Catalysts and Their Applications in Asymmetric Reactions
复制标题
苯基环丙烷基仲胺催化剂的设计合成及其在不对称反应中的应用
DOI：
10.1055/a-1796-7387
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发表时间：
2022
期刊：
影响因子：
2
通讯作者：
Takeshima Aika
中科院分区：
文献类型：
--
作者：
Kano Taichi;Takeshima Aika
大多数手性仲胺催化剂通常由手性氨基酸及其衍生物合成。另一方面，基于联萘骨架的胺催化剂先前已经被开发，并且在几个不对称反应中显示出独特的化学和立体选择性。然而，尽管它们的实用性，联萘基胺在不对称反应中的应用仍然很少，由于它们的合成效率低。在这种情况下，我们设计了胺催化剂具有苯基环丙烷骨架作为一种新的手性基序。这些新的催化剂可以容易地合成，并构建类似的联萘基胺催化剂的手性环境。此外，苯基环丙烷基氨基磺酰胺被发现是一种有效的催化剂，用于顺式选择性Mannich反应和使用炔基Z-酮亚胺的共轭加成。1引言2新型手性仲胺催化剂的设计和合成3苯基环丙烷基胺催化剂的性能评价4新型手性氨基磺酰胺催化的不对称反应的开发5结论
Most chiral secondary amine catalysts are usually synthesized from chiral amino acids and their derivatives. On the other hand, amine catalysts based on a binaphthyl backbone have previously been developed, and show unique chemo- and stereoselectivity in several asymmetric reactions. However, in spite of their utility, the applications of binaphthyl-based amines in asymmetric reactions are still rare due to their synthetic inefficiency. In this context, we have designed amine catalysts possessing a phenylcyclopropane scaffold as a novel chiral motif. These novel catalysts can be synthesized easily and construct a similar chiral environment to that of binaphthyl-based amine catalysts. In addition, a phenylcyclopropane-based amino sulfonamide is found to be an effective catalyst forsyn-selective Mannich reactions and conjugate additions using alkynylZ-ketimines.1 Introduction2 Design and Synthesis of Novel Chiral Secondary Amine Catalysts3 Performance Evaluation of Phenylcyclopropane-Based Amine Catalysts4 Development of Asymmetric Reactions Catalyzed by a Novel Chiral Amino Sulfonamide5 Conclusions