Enantioselective Thiolysis and Aminolysis of Cyclic Anhydrides Using a Chiral Diamine-Derived Thiourea Catalyst

被引：7

作者：

Shim, Jae Ho ^{[2
]}

Park, Sung Joo ^{[1
]}

Ahn, Byung Kook ^{[2
]}

Lee, Ji Yeon ^{[1
]}

Kim, Hyeon Soo ^{[2
]}

Ha, Deok-Chan ^{[1
]}

机构：

[1] Korea Univ, Dept Chem, Seoul 02841, South Korea

[2] Korea Univ, Coll Med, Dept Anat, Seoul 02842, South Korea

来源：

ACS OMEGA | 2021年 / 6卷 / 50期

基金：

新加坡国家研究基金会;

关键词：

ASYMMETRIC MICHAEL ADDITION; DESYMMETRIZATION; DERIVATIVES; DONORS;

D O I：

10.1021/acsomega.1c04741

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic desymmetrization of cyclic anhydrides has been widely investigated in the field of organocatalysis. Using this approach, many stereocenters can be established in a single, symmetry-breaking transformation. Herein, a thiourea organocatalyst was prepared in a single step from a chiral diamine, (R,R)-1,2-diphenylethylenediamine, and used for the desymmetrization of various cyclic anhydrides through double hydrogen-bonding activation. The asymmetric ring-opening reaction of the cyclic anhydride proceeded via the enantioselective addition reaction catalyzed by diamine thiourea. Thiolysis afforded the desired products in the yields of 86-98% and enantioselectivities of 60-94%, while aminolysis afforded the yields of 90-94% and enantioselectivities of 90-95%.

引用

页码：34501 / 34511

页数：11

共 42 条

[1] CATALYTIC ASYMMETRIC-SYNTHESIS OF HIGHLY FUNCTIONALIZED COMPOUNDS WITH 6 CONTIGUOUS STEREOCENTERS [J].