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

[31] Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes [J].

List, B ;

Pojarliev, P ;

Castello, C .

ORGANIC LETTERS, 2001, 3 (04) :573-575

[32]

LIST B, 2001, SYNLETT, P1901

[33] L-proline catalyzed asymmetric aldol reactions of protected hydroxyacetone [J].

Liu, HW ;

Peng, LZ ;

Zhang, T ;

Li, YL .

NEW JOURNAL OF CHEMISTRY, 2003, 27 (08) :1159-1160

[34] Total synthesis of cytotoxic macrolide amphidinolide B1 and the proposed structure of amphidinolide B2 [J].

Lu, Liang ;

Zhang, Wei ;

Carter, Rich G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7253-+

[35] Asymmetric bifunctional primary aminocatalysis on magnetic nanoparticles [J].

Luo, Sanzhong ;

Zheng, Xiaoxi ;

Cheng, Jin-Pei .

CHEMICAL COMMUNICATIONS, 2008, (44) :5719-5721

[36] Highly enantioselective direct syn- and anti-aldol reactions of dihydroxyacetones catalyzed by chiral primary amine catalysts [J].

Luo, Sanzhong ;

Xu, Hui ;

Zhang, Long ;

Li, Jiuyuan ;

Cheng, Jin-Pei .

ORGANIC LETTERS, 2008, 10 (04) :653-656

[37] A simple primary-tertiary diamine-Bronsted acid catalyst for asymmetric direct Aldol reactions of linear aliphatic ketones [J].

Luo, Sanzhong ;

Xu, Hui ;

Li, Jiuyuan ;

Zhang, Long ;

Cheng, Jin-Pei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3074-+

[38] Unusual reversal of regioselectivity in antibody-mediated aldol additions with unsymmetrical methyl ketones [J].

Maggiotti, V ;

Bahmanyar, S ;

Reiter, M ;

Resmini, M ;

Houk, KN ;

Gouverneur, V .

TETRAHEDRON, 2004, 60 (03) :619-632

[39]

Maggiotti V, 2002, ANGEW CHEM INT EDIT, V41, P1012, DOI 10.1002/1521-3773(20020315)41:6<1012::AID-ANIE1012>3.0.CO

[40]

2-I

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