C2-Symmetric Chiral Bisoxazolines as Hydrogen-Bond-Acceptor Catalysts in Enantioselective Aldol Reaction of β-Carbonyl Acids with Trifluoroacetaldehyde Hemiacetals

被引：28

作者：

Yang, Zhen-Yan ^{[1
,2
]}

Zeng, Jun-Liang ^{[1
,2
]}

Ren, Nan ^{[1
,2
]}

Meng, Wei ^{[3
]}

Nie, Jing ^{[1
,2
]}

Ma, Jun-An ^{[1
,2
]}

机构：

[1] Tianjin Univ, Tianjin Key Lab Mol Optoelect Sci, Dept Chem, Tianjin 300072, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China

[3] Chinese Acad Sci, Inst Chem, Beijing 100190, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC CATALYSIS; DECARBOXYLATIVE ADDITION; ETHYL HEMIACETAL; BIS(OXAZOLINE) LIGANDS; 3-HYDROXY OXINDOLES; KETOACIDS; ORGANOCATALYSIS; KETONES; ISATINS; COMPLEXES;

D O I：

10.1021/acs.orglett.6b03256

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple C-2-symmetric chiral bisoxazoline is demonstrated to use hydrogen bonding to catalyze an important family of aldol reactions of trifluoroacetaldehyde hemiacetals with various beta-carbonyl acids. This reaction is highly enantioselective, delivering chiral nonracemic trifluoromethylated alcohols with excellent optical purity and good isolated yields. This concept of relaying chiral information via a chiral hydrogen-bond acceptor should be applicable to a vast number of organo catalytic processes.

引用

页码：6364 / 6367

页数：4

共 49 条

[1] A first case of asymmetric catalysis induced by metal-free bisoxazolines [J].

Akalay, Deniz ;

Duerner, Gerd ;

Goebel, Michael W. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (14) :2365-2368

[2]

[Anonymous], 1960, The Nature of the Chemical Bond, 3rd ed

[3] Oxygen and nitrogen in competitive situations: Which is the hydrogen-bond acceptor? [J].

Bohm, HJ ;

Brode, S ;

Hesse, U ;

Klebe, G .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (12) :1509-1513

[4] Stereoarrayed CF3-Substituted 1,3-Diols by Dynamic Kinetic Resolution: Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation [J].

Cotman, Andrej Emanuel ;

Cahard, Dominique ;

Mohar, Barbara .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (17) :5294-5298

[5]

Dalko PI, 2013, COMPREHENSIVE ENANTIOSELECTIVE ORGANOCATALYSIS: CATALYSTS, REACTIONS, AND APPLICATIONS, VOLS 1-3, P1, DOI 10.1002/9783527658862

[6] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[7] Update 1 of: C2-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis [J].

Desimoni, Giovanni ;

Faita, Giuseppe ;

Jorgensen, Karl Anker .

CHEMICAL REVIEWS, 2011, 111 :PR284-PR437

[8]

Desiraju G.R., 1999, The Weak Hydrogen Bond

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

Doyle, Abigail G. ;

Jacobsen, Eric N. .

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

[10] A convenient enantioselective decarboxylative aldol reaction to access chiral α-hydroxy esters using β-keto acids [J].

Duan, Zhiqiang ;

Han, Jianlin ;

Qian, Ping ;

Zhang, Zirui ;

Wang, Yi ;

Pan, Yi .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :969-974

← 1 2 3 4 5 →