Highly Efficient Organocatalyzed Direct Asymmetric Aldol Reactions of Hydroxyacetone and Aldehydes

被引：45

作者：

Wu, Xiaoyu ^{[1
]}

Ma, Zhixiong ^{[2
]}

Ye, Zhengqing ^{[2
]}

Qian, Shan ^{[2
]}

Zhao, Gang ^{[2
]}

机构：

[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Organ Synthet Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 1-2期

关键词：

aldehydes; aldol reaction; 1,2-diols; hydroxyacetone; organic catalysis; WATER-COMPATIBLE ORGANOCATALYSTS; DIRECT SYN-ALDOL; UNPRECEDENTED REGIOCONTROL; BIOACTIVE MACROLIDES; L-PROLINE; KETONES; ACID; AMPHIDINOLIDES; STRATEGY; CATALYST;

D O I：

10.1002/adsc.200800558

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Novel organocatalysts derived from L-threonine and L-leucine have been synthesized for catalyzing direct aldol reactions of hydroxycetone and unactivated aliphatic aldehydes with as low as 2 mol% loading of the catalyst, good to excellent yields and excellent enantioselectivities have been achieved for aliphatic aldehydes, whereas aromatic aldehydes yield only moderate enantioselectivities.

引用

页码：158 / 162

页数：5

共 69 条

[1] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].

Allemann, C ;

Gordillo, R ;

Clemente, FR ;

Cheong, PHY ;

Houk, KN .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569

[2]

[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[3]

Benaglia M, 2001, ADV SYNTH CATAL, V343, P171, DOI 10.1002/1615-4169(20010226)343:2<171::AID-ADSC171>3.3.CO

[4]

2-V

[5]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[6] Synthesis of azasugars through a proline-catalyzed reaction [J].

Calderon, Felix ;

Doyaguez, Elisa G. ;

Fernandez-Mayoralas, Alfonso .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6258-6261

[7] Synthetic studies toward potent cytotoxic agents amphidinolides G and H:: Synthesis of the entire C15-C26 moiety of the top half [J].

Chakraborty, TK ;

Suresh, VR .

TETRAHEDRON LETTERS, 1998, 39 (42) :7775-7778

[8]

Chakraborty Tushar K., 2001, Current Medicinal Chemistry - Anti-Cancer Agents, V1, P131, DOI 10.2174/1568011013354660

[9] Organocatalyzed highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone and fluoroacetone in aqueous media: The use of water to control regioselectivity [J].

Chen, Xiao-Hua ;

Luo, Shi-Wei ;

Tang, Zhuo ;

Cun, Lin-Feng ;

Mi, Ai-Qiao ;

Jiang, Yao-Zhong ;

Gong, Liu-Zhu .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) :689-701

[10] Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides [J].

Cordova, Armando ;

Zou, Weibiao ;

Dziedzic, Pawel ;

Ibrahem, Ismail ;

Reyes, Efraim ;

Xu, Yongmei .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (20) :5383-5397

← 1 2 3 4 5 6 7 →