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铱催化氮杂环丁酮的不对称双烯丙基烷基化反应:高效构建手性 α-氨基酸衍生物。

Iridium-catalyzed asymmetric double allylic alkylation of azlactone: efficient access to chiral α-amino acid derivatives.

机构信息

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072, P. R. China.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, 230021, China.

出版信息

Chem Commun (Camb). 2022 Mar 3;58(19):3142-3145. doi: 10.1039/d2cc00328g.

Abstract

An unprecedented Ir-catalyzed enantioselective double allylic alkylation of less bulky cyclic imine glycinate (azlactone) was rationally designed and developed, providing various bisallylated chiral amino acid derivatives. Control experiments revealed that this transformation proceeds in a sequential manner featuring -dynamic kinetic resolution of the initially-formed monoallylation intermediates.

摘要

合理设计并发展了首例 Ir 催化的非位阻环状亚胺甘氨酸(氮丙啶酮)的对映选择性双烯丙基烷基化反应,提供了各种双烯丙基手性氨基酸衍生物。控制实验表明,该转化以顺序方式进行,最初形成的单烯丙基化中间体经历 -动态动力学拆分。

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