Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides,Synlett

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Scalable Synthesis of a Chiral Selenium π-Acid Catalyst and Its Use in Enantioselective Iminolactonization of β,γ-Unsaturated Amides
Synlett ( IF 1.7 ) Pub Date : 2019-06-28 , DOI: 10.1055/s-0039-1690109
Yuta Otsuka _{1,

2} , Yuto Shimazaki ₃ , Hitoshi Nagaoka ₃ , Keiji Maruoka _{3,

4} , Takuya Hashimoto _{1,

2,

3}

Affiliation

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 of N-methoxy β,γ-unsaturated amides to give iminolactones with high enantioselectivities.

中文翻译：

手性硒 π-酸催化剂的可扩展合成及其在 β,γ-不饱和酰胺的对映选择性亚胺内酯化中的应用

由于缺乏高对映选择性催化剂，手性硒 π-酸催化长期以来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，该催化剂以高对映选择性进行 β,γ-不饱和羧酸的氧化环化。我们在此报告了我们改进的这种手性硒催化剂的合成，它允许获得大量作为二硒化物的催化剂。此外，该催化剂在 N-甲氧基 β,γ-不饱和酰胺的氧化环化中进行了测试，以得到具有高对映选择性的亚氨基内酯。

更新日期：2019-06-28

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