Asymmetric SN1 α-Alkylation of Cyclic Ketones Catalyzed by Functionalized Chiral Ionic Liquid (FCIL) Organocatalysts

被引：78

作者：

Zhang, Long ^{[2
,3
]}

Cui, Lingyun ^{[1
]}

Li, Xin ^{[1
]}

Li, Jiuyuan ^{[1
]}

Luo, Sanzhong ^{[1
]}

Cheng, Jin-Pei ^{[2
,3
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

[2] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China

[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 07期

关键词：

alkylation; asymmetric catalysis; carbocations; chirality; ionic liquids; MICHAEL ADDITION; ALLYLIC ALKYLATION; HIGHLY EFFICIENT; ALDOL REACTION; ENANTIOSELECTIVE CYCLOPROPANATION; TRANSITION-METAL; PHASE-TRANSFER; ALDEHYDES; NUCLEOPHILICITY; PROLINE;

D O I：

10.1002/chem.200902509

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ionic liquid works better: The first intermolecular asymmetric α-alkylation of cyclic ketones was realized by using functionalized chiral ionic liquids as catalysts. The reaction proceeded with good to excellent yields and high ee. Highly stereoselective desymmetrization of 4-substituted cyclohexanones with >99:1 d.r. and up to 87 % ee were achieved by using this protocol. (Chemical Equation Representation). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA,.

引用

页码：2045 / 2049

页数：5

共 91 条

[1]

[Anonymous], 2008, ANGEW CHEM

[2] Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].

Baudequin, C ;

Brégeon, D ;

Levillain, J ;

Guillen, F ;

Plaquevent, JC ;

Gaumont, AC .

TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945

[3] Ionic liquids and chirality: opportunities and challenges [J].

Baudequin, C ;

Baudoux, J ;

Levillain, J ;

Cahard, D ;

Gaumont, AC ;

Plaquevent, JC .

TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093

[4] Enantioselective organocatalysis using SOMO activation [J].

Beeson, Teresa D. ;

Mastracchio, Anthony ;

Hong, Jun-Bae ;

Ashton, Kate ;

MacMillan, David W. C. .

SCIENCE, 2007, 316 (5824) :582-585

[5] Applications of chiral ionic liquids [J].

Bica, Katharina ;

Gaertner, Peter .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (19) :3235-3250

[6]

Braun M, 2000, ANGEW CHEM INT EDIT, V39, P3494, DOI 10.1002/1521-3773(20001002)39:19<3494::AID-ANIE3494>3.0.CO

[7]

2-4

[8]

Braun M., 2000, ANGEW CHEM, V112, P3637

[9]

Braun M., 2006, ANGEW CHEM, V118, P7106

[10] Tsuji-Trost allylic alkylation with ketone enolates [J].

Braun, Manfred ;

Meier, Thorsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :6952-6955

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