CuCl-catalyzed stereoselective conjugate addition of Grignard reagents to 2,3-allenoates

被引:4
作者
He, Jian [1 ]
Lu, Zhan [1 ]
Chai, Guobi [1 ]
Fu, Chunling [1 ]
Ma, Shengming [1 ]
机构
[1] Zhejiang Univ, Lab Mol Recognit & Synth, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
2,3-Allenoates; Grignard reagents; Copper-catalysis; Conjugate addition; CARBOCUPRATION;
D O I
10.1016/j.tet.2012.01.027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
CuCl was found to be an efficient catalyst for the conjugate addition of 2,3-allenoates with Grignard reagents to synthesize poly-substituted beta,gamma-unsaturated alkenoates with high stereoselectivity in good to excellent yields. Primary, secondary, and tertiary alkyl, vinyl or phenyl Grignard reagents may all be used. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2719 / 2724
页数:6
相关论文
共 20 条
[1]   Conjugate addition/Ireland-Claisen rearrangements of allyl fumarates: Simple access to terminally differentiated succinates [J].
Bausch, Cory C. ;
Johnson, Jeffrey S. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04) :1575-1577
[2]  
Berlan J., 1979, B SOC CHIM FR, VII, p[3, 183]
[3]  
Bryson T.A., 1977, TETRAHEDRON LETT, V18, P525
[4]   Ferric Chloride Hexahydrate-Catalyzed Highly Regio- and Stereoselective Conjugate Addition Reaction of 2,3-Allenoates with Grignard Reagents: An Efficient Synthesis of β,γ-Alkenoates [J].
Chai, Guobi ;
Lu, Zhan ;
Fu, Chunling ;
Ma, Shengming .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) :1946-1954
[5]   Copper-Catalyzed Conjugate Addition of Diboron Reagents to α,β-Unsaturated Amides: Highly Reactive Copper-1,2-Bis(diphenylphosphino)benzene Catalyst System [J].
Chea, Heesung ;
Sim, Hak-Suk ;
Yun, Jaesook .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (06) :855-858
[6]   Conjugate addition reactions of α-aminoalkylcuprates with α,β-alkenyl-, α,β-alkynyl-, α,β-β,γ-allenyl-, and α,β-γ,δ-dienyl carboxylie acid derivatives, nitriles, and sulfoxides [J].
Dieter, RK ;
Lu, K ;
Velu, SE .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8715-8724
[7]   Stereoselective synthesis of 4-alkylidene pyrrolidinones and pyrrolizidinones [J].
Dieter, RK ;
Lu, K .
TETRAHEDRON LETTERS, 1999, 40 (21) :4011-4014
[8]   sp2-sp3 Hybridized Mixed Diboron: Synthesis, Characterization, and Copper-Catalyzed β-Boration of α,β-Unsaturated Conjugated Compounds [J].
Gao, Ming ;
Thorpe, Steven B. ;
Santos, Webster L. .
ORGANIC LETTERS, 2009, 11 (15) :3478-3481
[9]   Vicinal Functionalization of Propiolate Esters via Catalytic Carbocupration: Stereoselective Formation of Substituted Vinyl Silanes [J].
Hendrix, Amanda J. Mueller ;
Jennings, Michael P. .
ORGANIC LETTERS, 2010, 12 (12) :2750-2753
[10]   Synthesis of δ-lactones from 2-alkynyl epoxides and 4-alkynyl-1,3-dioxolan-2-ones by palladium catalysed carbonylation and conjugate nucleophilic addition [J].
Knight, JG ;
Ainge, SW ;
Baxter, CA ;
Eastman, TP ;
Harwood, SJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (19) :3188-3190