Catalytic Enantioselective Aldol Additions to Ketones

被引：55

作者：

Adachi, Shinya ^{[1
]}

Harada, Toshiro ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 22期

关键词：

Aldol reactions; Asymmetric catalysis; Asymmetric synthesis; Ketones; C-2-SYMMETRIC COPPER(II) COMPLEXES; QUATERNARY CARBON CENTERS; CHIRAL LEWIS-ACIDS; C BOND FORMATION; REDUCTIVE ALDOL; ASYMMETRIC ALDOL; REFORMATSKY REACTION; CONJUGATE REDUCTION; MICHAEL ADDITION; ACYCLIC ENONES;

D O I：

10.1002/ejoc.200900166

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective aldol addition to ketones has received growing attention since the resulting tertiary aldols are valuable building blocks for many biologically active compounds. Recently, several catalytic methodologies have been developed based on the activation of acceptor ketones and/or nucleophile enolates, overcoming problems associated with the lower reactivity and decreased steric discrimination of ketones compared to aldehydes. This microreview presents an overview of the progresses in the catalytic enantioselective aldol additions to ketones. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：3661 / 3671

页数：11

共 135 条

[81] Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents [J].

List, B .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :548-557

[82] Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine [J].

Liu, Jie ;

Yang, Zhigang ;

Wang, Zhen ;

Wang, Fei ;

Chen, Xiaohong ;

Liu, Xiaohua ;

Feng, Xiaoming ;

Su, Zhishan ;

Hu, Changwei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5654-+

[83]

Mahrwald R., 2004, Modern Aldol Reactions, DOI DOI 10.1002/9783527619566

[84] Magnesium chloride-promoted Michael addition of dimethylsilyl enolates to α-enones [J].

Miura, K ;

Nakagawa, T ;

Hosomi, A .

SYNLETT, 2003, (13) :2068-2070

[85]

Miura K, 2000, ANGEW CHEM INT EDIT, V39, P1958, DOI 10.1002/1521-3773(20000602)39:11<1958::AID-ANIE1958>3.0.CO

[86]

2-4

[87] Uncatalyzed aldol reaction using a dimethylsilyl enolate and α-dimethylsilyl ester in N,N-dimethylformamide [J].

Miura, K ;

Sato, H ;

Tamaki, K ;

Ito, H ;

Hosomi, A .

TETRAHEDRON LETTERS, 1998, 39 (17) :2585-2588

[88]

Miura K., 2000, ANGEW CHEM, V112, P2034

[89] Catalytic and asymmetric vinylogous mukaiyama reactions on aliphatic ketones:: Formal asymmetric synthesis of taurospongin A [J].

Moreau, X ;

Bazán-Tejeda, B ;

Campagne, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7288-7289

[90] Conjugate reduction of α,β-unsaturated ketones with hydrosilane mediated by copper(I) salt [J].

Mori, A ;

Fujita, A ;

Kajiro, H ;

Nishihara, Y ;

Hiyama, T .

TETRAHEDRON, 1999, 55 (15) :4573-4582

← 4 5 6 7 8 9 10 11 12 13 →