Recent Advances in Metal-Catalyzed 1,2-Difunctionalization of Conjugated Dienes

被引:57
作者
Wu, Zhengxing [1 ]
Zhang, Wanbin [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
metal-catalyzed; conjugated diene; 1,2-difunctionalization; ASYMMETRIC HECK REACTION; CU(I)-CATALYZED REGIOSELECTIVE DIAMINATION; VICINAL DIAMINATION; 1,3-DIENES; ARYL; ALKENES; HETEROANNULATION; OXYAMINATION; DERIVATIVES; REACTIVITY;
D O I
10.6023/cjoc201704031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,2-difunctionalization of conjugated dienes is an important homogeneous catalytic reaction. The obtained products through 1,2-difunctionalization are widely existed in natural products and bioactive compounds, and are also sources of important organic intermediates, in addition, the preserved double bond in the difunctionalized product can be further transformed to give the desired structures or be functionalized sequentially to achieve multi-functionalization. The main difficulties focus on the encountered complex selectivities, including the regioselectivity, chemoselectivity and stereoselectivity in reactions. In recent years, with the development of organometallic chemistry, metal palladium, copper, iron or silver catalyzed 1,2-difunctionalizations of conjugated dienes have been reported in succession. In some cases the enantioselective 1,2-difunctionalizations of conjugated dienes were achieved via the introduction of chiral ligands. This review mainly focus on the recent metal catalyzed 1,2-difunctionalizations of conjugated dienes.
引用
收藏
页码:2250 / 2262
页数:13
相关论文
共 77 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   Palladium-catalyzed 1,4-acetoxy-trifluoroacetoxylation and 1,4-alkoxy-trifluoroacetoxylation of cyclic 1,3-dienes.: Scope and mechanism [J].
Aranyos, A ;
Szabó, KJ ;
Bäckvall, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2523-2529
[3]  
Backvall J.-E., 2010, MODERN OXIDATION MET
[4]  
BACKVALL JE, 1980, J ORG CHEM, V45, P2893
[5]  
BACKVALL JE, 1978, TETRAHEDRON LETT, P163
[6]   Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes [J].
Bar, GLJ ;
Lloyd-Jones, GC ;
Booker-Milburn, KI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7308-7309
[7]   Osmium-free direct syn-dihydroxylation of alkenes [J].
Bataille, Carole J. R. ;
Donohoe, Timothy J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) :114-128
[8]   trans-1,2-diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: Applications in asymmetric synthesis and molecular recognition [J].
Bennani, YL ;
Hanessian, S .
CHEMICAL REVIEWS, 1997, 97 (08) :3161-3195
[9]   The synthesis of vicinal amino alcohols [J].
Bergmeier, SC .
TETRAHEDRON, 2000, 56 (17) :2561-2576
[10]   Asymmetric 1,4-Dihydroxylation of 1,3-Dienes by Catalytic Enantioselective Diboration [J].
Burks, Heather E. ;
Kliman, Laura T. ;
Morken, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (26) :9134-+