Silver-Catalyzed Reaction of Enynals with Alkenes: A Tandem 1,3-Dipolar Cycloaddition/Cyclopropanation

被引:67
作者
Liang, Renxiao [1 ]
Ma, Tongmei [1 ]
Zhu, Shifa [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中央高校基本科研业务费专项资金资助;
关键词
AZA-COPE REARRANGEMENTS; ORGANOMETALLIC COMPOUNDS; THERMAL-DECOMPOSITION; CYCLIZATION REACTIONS; EFFICIENT SYNTHESIS; CARBENE INSERTION; VINYLIC COPPER(I); BOND; ALLENES; FURANS;
D O I
10.1021/ol5017299
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A silver-catalyzed reaction of enynals with alkenes to synthesize a series of polycyclic compounds has been developed. The reaction occurred smoothly using enynals with electron-deficient alkynes or terminal alkynes as substrates. The reaction was proposed to proceed through a tandem 1,3-dipolar cycloaddition/cyclopropanation process. The preliminary investigations of the asymmetric catalytic version revealed that the biphosphine ligand could be used as the potential efficient chiral ligand.
引用
收藏
页码:4412 / 4415
页数:4
相关论文
共 48 条
[1]   Silver-mediated synthesis of heterocycles [J].
Alvarez-Corral, Miriam ;
Munoz-Dorado, Manuel ;
Rodirguez-Garcia, Ignacio .
CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198
[2]   Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines [J].
Asao, N ;
Yudha, S ;
Nogami, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5526-5528
[3]  
Brummer O., 2001, CHEM COMMUN, P19
[4]   Activation of alkyl halides via a silver-catalyzed carbene insertion process [J].
Dias, HVR ;
Browning, RG ;
Polach, SA ;
Diyabalanage, HVK ;
Lovely, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9270-9271
[5]   Copper, silver and gold-based catalysts for carbene addition or insertion reactions [J].
Díaz-Requejo, MM ;
Pérez, PJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5441-5450
[6]   Mechanism of silver-mediated di-tert-butylsilylene transfer from a silacyclopropane to an alkene [J].
Driver, TG ;
Woerpel, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :9993-10002
[7]   Reactions of group IV R4M compounds with silver and copper salts [J].
Gilman, H ;
Woods, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :435-437
[8]  
Ha J.D., 1999, J AM CHEM SOC, V121, P10012
[9]  
Halbes-Letinois U, 2007, CHEM SOC REV, V36, P759, DOI 10.1039/b602151b
[10]  
Harmata M., 2010, SILVER ORGANIC CHEM