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 50 条

[1] Organocatalyzed highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone and fluoroacetone in aqueous media: The use of water to control regioselectivity
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
[2] Asymmetric Organocatalyzed Direct Aldol Additions of Enolizable Aldehydes
Scheffler, Ulf
Mahrwald, Rainer
SYNLETT, 2011, (12) : 1660 - 1667
[3] Trifluoromethylated-Imidazolines as Efficient Organocatalyst for Asymmetric Aldol Reaction of Hydroxyacetone with Aldehydes
Xie, Xiaojuan
Zhang, Zhong
Zhao, Huaxin
Wan, Wen
Hao, Jian
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (01) : 117 - 121
[4] Direct catalytic asymmetric aldol reactions of aldehydes
Bogevig, A
Kumaragurubaran, N
Jorgensen, KA
CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
[5] Highly efficient asymmetric direct stoichiometric aldol reactions on/in water
Huang, Junmin
Zhang, Xiaotong
Armstrong, Daniel W.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (47) : 9073 - 9077
[6] Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: Unprecedented regiocontrol in aqueous media
Tang, Z
Yang, ZH
Cun, LF
Gong, LZ
Mi, AQ
Jiang, YZ
ORGANIC LETTERS, 2004, 6 (13) : 2285 - 2287
[7] Direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones
Yamada, YMA
Yoshikawa, N
Sasai, H
Shibasaki, M
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (17) : 1871 - 1873
[8] Telaprevir fragments as organocatalysts in asymmetric direct aldol reactions of aldehydes
Chen Chen Weng
Xinliang Xu
Xiao Xia Xiong
Xiu Lian Lu
Yi Feng Zhou
Russian Journal of General Chemistry, 2013, 83 : 2447 - 2452
[9] Direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones
Graduate Sch. of Pharmaceut. Sci., University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan
Angew Chem (Int Ed Engl), 17 (1871-1873):
[10] Telaprevir fragments as organocatalysts in asymmetric direct aldol reactions of aldehydes
Weng, Chen Chen
Xu, Xinliang
Xiong, Xiao Xia
Lu, Xiu Lian
Zhou, Yi Feng
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2013, 83 (12) : 2447 - 2452

← 1 2 3 4 5 →