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

页码：87 / 146

页数：60

共 207 条

[81] Palladium(II)-catalyzed SN2′ reactions of α-allenic acetates.: Stereoconvergent synthesis of (Z,E)-2-bromo-1,3-dienes [J].

Horváth, A ;

Bäckvall, JE .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8120-8126

[82] Highly regio- and stereoselective intermolecular tandem reaction to synthesize chloro-substituted 1,3-butadienes [J].

Huang, Jing-Mei ;

Dong, Yi ;

Wang, Xu-Xiao ;

Luo, Hui-Chao .

CHEMICAL COMMUNICATIONS, 2010, 46 (07) :1035-1037

[83] Gold-Catalyzed Stereocontrolled Synthesis of 2,3-Bis(acetoxy)-1,3-dienes [J].

Huang, Xiaogen ;

de Haro, Teresa ;

Nevado, Cristina .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (24) :5904-5908

[84] Highly stereo- and regioselective synthesis of (Z)-trisubstituted Alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling [J].

Huang, Zhihong ;

Negishi, Ei-ichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) :14788-14792

[85] Catalytic reductive coupling of alkenes and alkynes to carbonyl compounds and imines mediated by hydrogen [J].

Iida, Hiroki ;

Krische, Michael J. .

METAL CATALYZED REDUCTIVE C-C BOND FORMATION: A DEPARTURE FROM PREFORMED ORGANOMETALLIC REAGENTS, 2007, 279 :77-104

[86] Transition metal-catalyzed ring-opening, substitution, and cyclopropanation reactions via vinylcarbene complexes generated from O-propargyl thiocarbamates [J].

Ikeda, Yuji ;

Murai, Masahito ;

Abo, Tomohiro ;

Miki, Koji ;

Ohe, Kouichi .

TETRAHEDRON LETTERS, 2007, 48 (38) :6651-6654

[87] β-Olefination of 2-Alkynoates Leading to Trisubstituted 1,3-Dienes [J].

Jacobsen, Mathias J. ;

Funder, Erik Daa ;

Cramer, Jacob R. ;

Gothelf, Kurt V. .

ORGANIC LETTERS, 2011, 13 (13) :3418-3421

[88]

JEFFERY T, 1987, SYNTHESIS-STUTTGART, P70

[89] Direct, stereospecific generation of (Z)-disubstituted allylic alcohols [J].

Jeon, Sang-Jin ;

Fisher, Ethan L. ;

Carroll, Patrick J. ;

Walsh, Patrick J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9618-9619

[90] Regio- and Stereoselective Synthesis of Multisubstituted Olefins and Conjugate Dienes by Using α-Oxo Ketene Dithioacetals as the Building Blocks [J].

Jin, Weiwei ;

Du, Wangming ;

Yang, Qin ;

Yu, Haifeng ;

Chen, Jiping ;

Yu, Zhengkun .

ORGANIC LETTERS, 2011, 13 (16) :4272-4275

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