Organocatalytic Enantioselective and Diastereodivergent Mannich Reactions of 5-Substituted Oxazolidin-2,4-Diones

被引：0

作者：

Yin, Yanli ^{[1
,4
]}

Fan, Yifan ^{[2
]}

Zhao, Xiaowei ^{[2
]}

Chai, Guobi ^{[3
]}

Jiang, Zhiyong ^{[2
,4
]}

机构：

[1] Henan Univ Technol, Coll Bioengn, Zhengzhou 450001, Henan, Peoples R China

[2] Henan Univ, Int Sci & Technol Cooperat Base Chiral Chem, Jinming Campus, Kaifeng 475004, Henan, Peoples R China

[3] Zhengzhou Tobacco Res Inst CNTC, Key Lab Tobacco Flavor Basic Res CNTC, Zhengzhou 450001, Henan, Peoples R China

[4] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 10卷 / 10期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

Asymmetric organocatalysis; Hydrogen-bonding catalysis; Mannich reaction; Oxazolidin-2; 4-diones; Diastereodivergence; ADDITION-PROTONATION; CONJUGATE ADDITION; DUAL CATALYSIS; ACID; 2,4-OXAZOLIDINEDIONE; 5H-OXAZOL-4-ONES; DERIVATIVES; KETONES;

D O I：

10.1002/ajoc.202100480

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric Mannich reaction of 5-substituted oxazolidine-2,4-diones is reported. By using an L-tert-leucine-derived thiourea-tertiary amine as catalyst, a variety of valuable oxazolidine-2,4-ones bearing a quaternary stereocenter at the 5-position and an adjacent aza-tertiary stereocenter at the alpha-position of the heterocycles were obtained in high enantio- and diastereoselectivities. Meanwhile, exploiting an L-tert-leucine-derived dipeptide-based thiourea-amide-tertiary amine catalyst could switch diastereoselectivity, delivering the corresponding diastereomers with good to excellent enantioselectivities.

引用

页码：2538 / 2543

页数：6

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