Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides
Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides
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手性硒 π 酸催化剂的可规模合成及其在 β,γ-不饱和酰胺对映选择性亚氨基内酯化反应中的应用
DOI：
10.1055/s-0039-1690109
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发表时间：
2019
期刊：
影响因子：
2
通讯作者：
and T. Hashimoto
中科院分区：
文献类型：
--
作者：
Y. Otsuka;Y. Shimazaki;H. Nagaoka;K. Maruoka;and T. Hashimoto
由于缺乏高对映选择性的催化剂，手性硒π酸催化一直落后于其他不对称催化领域。在这方面，我们最近开发了第一个手性硒π酸催化剂，用于高对映选择性的β，γ-不饱和羧酸的氧化环化。我们在此报告了我们改进的手性硒催化剂的合成，它允许获得大量的催化剂作为二硒化物。此外，还测试了该催化剂对n -甲氧基β，γ-不饱和酰胺的氧化环化反应，得到具有高对映选择性的亚胺内酯。
Chiral selenium π-acid catalysis has for a long time been lagging behind other areas of asymmetric catalysis due to a lack of highly enantioselective catalysts. In this regard, we recently developed the first chiral selenium π-acid catalyst which performs the oxidative cyclization of β,γ-unsaturated carboxylic acids with high enantioselectivities. We report herein our improved synthesis of this chiral selenium catalyst, which allows access to a large quantity of the catalyst as the diselenide. In addition, the catalyst is tested in the oxidative cyclization ofN-methoxy β,γ-unsaturated amides to give iminolactones with high enantioselectivities.