New Prolinamides with Isosteviol Skeleton as Efficient Organocatalysts for the Direct Asymmetric Aldol Reaction

被引：5

作者：

Liu, Yu-Xia ^{[1
]}

Ma, Zhi-Wei ^{[3
]}

Li, Yan-Xun ^{[1
]}

Tao, Jing-Chao ^{[2
]}

机构：

[1] Henan Inst Engn, Dept Mat & Chem Engn, Zhengzhou 450007, Henan, Peoples R China

[2] Zhengzhou Univ, Dept Chem, New Drug Res & Dev Ctr, Zhengzhou 450052, Henan, Peoples R China

[3] Henan Univ Anim Husb & Econ, Dept Fundamental Courses, Zhengzhou 450044, Henan, Peoples R China

来源：

LETTERS IN ORGANIC CHEMISTRY | 2018年 / 15卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Aldol reaction; asymmetric catalysis; isosteviol; organocatalyst; prolinamide; synthesis; 3-COMPONENT MANNICH REACTIONS; MICHAEL ADDITION; STEREOSELECTIVE-SYNTHESIS; AQUEOUS-MEDIUM; WATER; DERIVATIVES; CATALYSIS; ALDEHYDES; KETONES; ISOBUTYRALDEHYDE;

D O I：

10.2174/1570178615666171226163338

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this work, two new prolinamides with isosteviol skeleton were synthesized and used as chiral catalysts for the asymmetric aldol reaction. Solvent effects, catalyst loading, substrate scope and the influence of water on the reaction were investigated. With only 5 mol % loading, the synthesized catalysts showed excellent activity (up to 98% yield) and good stereoselectivity (up to 87:13 dr, 90% ee) for the direct aldol reaction of cyclohexanone and substituted benzaldehydes at room temperature.

引用

页码：307 / 313

页数：7

共 32 条

[1] A Simple Recipe for Sophisticated Cocktails: Organocatalytic One-Pot Reactions-Concept, Nomenclature, and Future Perspectives [J].

Albrecht, Lukasz ;

Jiang, Hao ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8492-8509

[2] Isosteviol?Proline Conjugates as Highly Efficient Amphiphilic Organocatalysts for Asymmetric Three-Component Mannich Reactions in the Presence of Water [J].

An, Ya-Jie ;

Wang, Chuan-Chuan ;

Liu, Zi-Ping ;

Tao, Jing-Chao .

HELVETICA CHIMICA ACTA, 2012, 95 (01) :43-51

[3] Highly Enantioselective α-aminoxylation Reactions Catalyzed by Isosteviol-proline Conjugates in Buffered Aqueous Media [J].

An, Ya-Jie ;

Wang, Chuan-Chuan ;

Xu, Yuan-Zhen ;

Wang, Wei-Juan ;

Tao, Jing-Chao .

CATALYSIS LETTERS, 2011, 141 (08) :1123-1129

[4] Simple amphiphilic isosteviol-proline conjugates as chiral catalysts for the direct asymmetric aldol reaction in the presence of water [J].

An, Ya-Jie ;

Zhang, Yun-Xiao ;

Wu, Ya ;

Liu, Zhao-Min ;

Pi, Chao ;

Tao, Jing-Chao .

TETRAHEDRON-ASYMMETRY, 2010, 21 (06) :688-694

[5] Isosteviol-amino Acid Conjugates as Highly Efficient Organocatalysts for the Asymmetric One-pot Three-component Mannich Reactions [J].

An Yajie ;

Qin Qian ;

Wang Chuanchuan ;

Tao Jingchao .

CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (07) :1511-1517

[6] Organocatalytic Enantioselective α-Hydroxymethylation of Aldehydes: Mechanistic Aspects and Optimization [J].

Boeckman, Robert K., Jr. ;

Biegasiewicz, Kyle F. ;

Tusch, Douglas J. ;

Miller, John R. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) :4030-4045

[7] Organocatalytic Asymmetric Michael Addition of Aliphatic Aldehydes to Indolylnitroalkenes: Access to Contiguous Stereogenic Tryptamine Precursors [J].

Chen, Jian ;

Geng, Zhi-Cong ;

Li, Ning ;

Huang, Xiao-Fei ;

Pan, Feng-Feng ;

Wang, Xing-Wang .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) :2362-2372

[8] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[9] Highly enantioselective α-aminoxylation of aldehydes and ketones with a polymer-supported organocatalyst [J].

Font, Daniel ;

Bastero, Amaia ;

Sayalero, Sonia ;

Jimeno, Ciril ;

Pericas, Miquel A. .

ORGANIC LETTERS, 2007, 9 (10) :1943-1946

[10] A highly active 4-siloxyproline catalyst for asymmetric synthesis [J].

Hayashi, Y ;

Yamaguchi, J ;

Hibino, K ;

Sumiya, T ;

Urushima, T ;

Shoji, M ;

Hashizume, D ;

Koshino, H .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (12) :1435-1439

← 1 2 3 4 →