Dinuclear zinc catalyzed asymmetric tandem Michael addition/acetalization reactions of cyclic diketones and β,γ-unsaturated α-ketoesters

被引：23

作者：

Song, Xixi ^{[1
]}

Liu, Jing ^{[1
]}

Liu, Meng-Meng ^{[1
]}

Wang, Xi ^{[1
]}

Zhang, Zhao-Fei ^{[1
]}

Wang, Min-Can ^{[1
]}

Chang, Junbiao ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Henan, Peoples R China

来源：

TETRAHEDRON | 2014年 / 70卷 / 35期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

Asymmetric catalysis; Michael addition; Dinuclear zinc complex; Tandem reaction; Oxygen heterocycles; ALPHA; BETA-UNSATURATED N-ACYLPYRROLES; 6-MEMBERED OXYGENATED HETEROCYCLES; BOND-FORMING REACTIONS; 1,3-DICARBONYL COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITIONS; PHOSPHINE OXIDES; KETO ESTERS; NITROALKENES; DERIVATIVES;

D O I：

10.1016/j.tet.2014.06.109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dinuclear zinc-ProPhenol complex is applied as efficient catalyst in the highly stereoselective tandem Michael addition/acetalization reactions of cyclic 1,3-diketones and beta,gamma-unsaturated alpha-ketoesters. A variety of substrates are well-tolerated, and a broad range of synthetically and pharmaceutically useful chiral chromene derivatives are directly produced in good yields of up to 96% and good enantioselectivities of up to 96% ee. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5468 / 5474

页数：7

共 31 条

[1] Catalytic, Asymmetric Michael Reactions of Cyclic Diketones with β,γ-Unsaturated α-Ketoesters [J].

Calter, Michael A. ;

Wang, Jun .

ORGANIC LETTERS, 2009, 11 (10) :2205-2208

[2] Catalytic asymmetric carbon-carbon bond forming reactions catalyzed by tetrahydroisoquinoline (TIQ) N,N′-dioxide ligands [J].

Cele, Zamani E. D. ;

Sosibo, Sphelele C. ;

Andersson, Pher G. ;

Kruger, Hendrik G. ;

Maguire, Glenn E. M. ;

Govender, Thavendran .

TETRAHEDRON-ASYMMETRY, 2013, 24 (04) :191-195

[3] Highly Enantioselective Michael Addition of Cyclic 1,3-Dicarbonyl Compounds to β,γ-Unsaturated α-Keto Esters [J].

Chen, Xing-Kuan ;

Zheng, Chang-Wu ;

Zhao, Sheng-Li ;

Chai, Zhuo ;

Yang, Ying-Quan ;

Zhao, Gang ;

Cao, Wei-Guo .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1648-1652

[4] Strategies for the formation of tetrahydropyran rings in the synthesis of natural products [J].

Clarke, Paul A. ;

Santos, Soraia .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) :2045-2053

[5] Substituted (E)-2-Oxo-3-butenoates: Reagents for Every Enantioselectively-Catalyzed Reaction [J].

Desimoni, Giovanni ;

Faita, Giuseppe ;

Quadrelli, Paolo .

CHEMICAL REVIEWS, 2013, 113 (08) :5924-5988

[6] N,N′-Dioxide-nickel(II) complex catalyzed asymmetric Michael addition of cyclic 1,3-dicarbonyl compounds to β,γ-unsaturated α-ketoesters [J].

Dong, Zhenhua ;

Feng, Juhua ;

Cao, Weidi ;

Liu, Xiaohua ;

Lin, Lili ;

Feng, Xiaoming .

TETRAHEDRON LETTERS, 2011, 52 (27) :3433-3436

[7] Highly Enantioselective Conjugate Addition of Cyclic Diketones to β,γ-Unsaturated α-Ketoesters Catalyzed by an N,N′-Dioxide-Cu(OTf)2 Complex [J].

Dong, Zhenhua ;

Feng, Juhua ;

Fu, Xuan ;

Liu, Xiaohua ;

Lin, Lili ;

Feng, Xiaoming .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (04) :1118-1121

[8] Structure-Activity Relationship Study of First Selective Inhibitor of Excitatory Amino Acid Transporter Subtype 1: 2-Amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101) [J].

Erichsen, Mette N. ;

Huynh, Tri H. V. ;

Abrahamsen, Bjarke ;

Bastlund, Jesper F. ;

Bundgaard, Christoffer ;

Monrad, Olja ;

Bekker-Jensen, Anders ;

Nielsen, Christina W. ;

Frydenvang, Karla ;

Jensen, Anders A. ;

Bunch, Lennart .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) :7180-7191

[9] Enantioselective Synthesis of Coumarins Catalyzed by a Bifunctional Amine-Thiourea Catalyst [J].

Gao, Yaojun ;

Ren, Qiao ;

Wang, Lei ;

Wang, Jian .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (44) :13068-13071

[10] Direct asymmetric Michael reactions of cyclic 1,3-dicarbonyl compounds and enamines catalyzed by chiral bisoxazoline-copper(II) complexes [J].

Halland, N ;

Velgaard, T ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5067-5074

← 1 2 3 4 →