Dipeptidic Proline-Derived Thiourea Organocatalysts for Asymmetric Michael addition Reactions between Aldehydes and Nitroolefins

被引：1

作者：

Yeo, Hyoung Min ^{[1
]}

Kim, Taek Hyeon ^{[1
]}

机构：

[1] Chonnam Natl Univ, Coll Engn, Sch Chem Engn, Gwangju 61186, South Korea

来源：

CHEMISTRYSELECT | 2024年 / 9卷 / 32期

基金：

新加坡国家研究基金会;

关键词：

Bifunctional organocatalyst; Dipeptide proline amide-thiourea; Asymmetric conjugate addition of aldehydes and nitroalkenes; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; CARBONYL-COMPOUNDS; ENAMINE CATALYSIS; ALDOL REACTIONS; KETONES; EFFICIENT; DERIVATIVES; ENTRY;

D O I：

10.1002/slct.202402694

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantiodivergent synthesis of syn-Michael adducts can be easily achieved by switching the terminal proline in dipeptidic proline-thiourea catalysts. In this study, a dipeptidic proline-derived thiourea organocatalyst was rationally designed and facilely prepared from dipeptidic proline, a chiral diamine as a linker, and isothiocyanate. This asymmetric bifunctional catalyst for Michael addition between aldehydes and nitroolefins provided chiral 4-nitro aldehyde adducts with yields of up to 99 %, 92 : 8 syn-diastereoselectivity, and 97 % enantiomeric excess at room temperature. A chiral dipeptidic proline-derived thiourea organocatalyst was rationally designed and facilely prepared from dipeptidic proline, a chiral diamine as a linker, and isothiocyanate. This asymmetric catalyst for Michael addition between aldehydes and nitroolefins provided chiral 4-nitro aldehyde adducts with yields of up to 99 %, 92 : 8 syn-diastereoselectivity, and 97 % enantiomeric excess at room temperature. image

引用

页数：7

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