Recent Advances in Stereoselective Synthesis of 1,3-Dienes

被引:116
作者
De Paolis, Michael [1 ]
Chataigner, Isabelle [1 ]
Maddaluno, Jacques [1 ]
机构
[1] Univ Rouen, UMR CNRS COBRA 6014, F-76821 Mont St Aignan, France
来源
STEREOSELECTIVE ALKENE SYNTHESIS | 2012年 / 327卷
关键词
Conjugated dienes; Ene-ene coupling; Ene-yne coupling; Isomerization; Organocatalysis; Stereoselective synthesis; Transition metals; Yne-yne coupling; CROSS-COUPLING REACTION; CATALYZED REDUCTIVE COUPLINGS; BOND-FORMING HYDROGENATION; CONJUGATED DIENOIC ESTERS; STEREOCONTROLLED SYNTHESIS; REGIOSELECTIVE-SYNTHESIS; SELECTIVE SYNTHESIS; ALKYLIDENE COMPLEXES; EFFICIENT SYNTHESIS; CARBON-CARBON;
D O I
10.1007/128_2012_320
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aim of this review is to present the latest developments in the stereoselective synthesis of conjugated dienes, covering the period 2005-2010. Since the use of this class of compounds is linked to the nature of their appendages (aryls, alkyls, electron-withdrawing, and heterosubstituted groups), the review has been categorized accordingly and illustrates the most representative strategies and mechanisms to access these targets.
引用
收藏
页码:87 / 146
页数:60
相关论文
共 207 条
[101]   The phosphine-catalyzed alkyne to 1,3-diene isomerization reaction [J].
Kwong, Cathy Kar-Wing ;
Fu, Michael Yunyi ;
Lam, Cynthia Sze-Lok ;
Toy, Patrick H. .
SYNTHESIS-STUTTGART, 2008, (15) :2307-2317
[102]  
Langer P, 2002, SYNTHESIS-STUTTGART, P441
[103]   Palladium-tetraphosphine complex catalysed Heck reaction of vinyl bromides with alkenes: A powerful access to conjugated dienes [J].
Lemhadri, Mhamed ;
Battace, Ahmed ;
Berthiol, Florian ;
Zair, Touriya ;
Doucet, Henri ;
Santelli, Maurice .
SYNTHESIS-STUTTGART, 2008, (07) :1142-1152
[104]   Au-catalyzed synthesis of (1Z,3E)-2-pivaloxy-1,3-dienes from propargylic pivalates [J].
Li, Guotao ;
Zhang, Guozhu ;
Zhang, Liming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) :3740-+
[105]   Palladium-catalyzed intermolecular ene-yne coupling: Development of an atom-efficient Mizoroki-Heck-type reaction [J].
Lindhardt , Anders T. ;
Mantel, Mette Louise H. ;
Skrydstrup, Troels .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) :2668-2672
[106]   Solvent-free heterogeneous organocatalysis:: stereoselective isomerization of α,β-ynones to (E,E)-α,β-γ,δ-dienones catalyzed by polymer-supported tertiaryphosphines [J].
Liu, Hai-Ling ;
Jiang, Huan-Feng ;
Xu, Lin ;
Zhan, Hai-Ying .
TETRAHEDRON LETTERS, 2007, 48 (47) :8371-8375
[107]   Highly convergent, stereospecific synthesis of 11-cis-retinoids by metal-catalyzed cross-coupling reactions of (Z)-1-alkenylmetals [J].
Lopez, Susana ;
Montenegro, Javier ;
Saa, Carlos .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9572-9581
[108]   HIGHLY STEREOSELECTIVE ISOMERIZATION OF YNONES TO CONJUGATED DIENONES CATALYZED BY TRANSITION-METAL COMPLEXES [J].
MA, DW ;
YU, YH ;
LU, XY .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1105-1109
[109]   Phosphine-mediated diverse reactivity of γ-substituted allenoates with aldehydes: syntheses of highly functionalized chromans and (E,E)-1,3-dienes [J].
Ma, Renqin ;
Xu, Silong ;
Tang, Xiaofang ;
Wu, Guiping ;
He, Zhengjie .
TETRAHEDRON, 2011, 67 (06) :1053-1061
[110]   Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes [J].
Mahandru, GM ;
Liu, G ;
Montgomery, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3698-3699