Synthesis of lactams via copper-catalyzed intramolecular vinylation of amides

被引:120
作者
Hu, TS [1 ]
Li, CZ [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ol0505555
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed intramolecular vinylation of iodoenamides were investigated for the first time. With Cul as the catalyst and N,N-dimethylethylenediamine as the ligand, a number of iodoenamides underwent cyclization in dioxane leading to the formations of five- to seven-membered lactams in moderate to excellent yields.
引用
收藏
页码:2035 / 2038
页数:4
相关论文
共 43 条
[1]   Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].
Antilla, JC ;
Baskin, JM ;
Barder, TE ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587
[2]   Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950 [J].
Coleman, RS ;
Liu, PH .
ORGANIC LETTERS, 2004, 6 (04) :577-580
[3]   Stereocontrolled synthesis of the diene and triene macrolactones of oximidines I and II: Organometallic coupling versus standard macrolactonization [J].
Coleman, RS ;
Garg, R .
ORGANIC LETTERS, 2001, 3 (22) :3487-3490
[4]  
COSSY J, 1943, EUR J ORG CHEM, V8, P1925
[5]   Mild conditions for copper-catalysed N-arylation of pyrazoles [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709
[6]   Amino acid-mediated Goldberg reactions between amides and aryl iodides [J].
Deng, W ;
Wang, YF ;
Zou, W ;
Liu, L ;
Guo, QX .
TETRAHEDRON LETTERS, 2004, 45 (11) :2311-2315
[7]   THE REACTION OF IODOTRIMETHYLSILANE WITH ACETYLENIC ALCOHOLS [J].
GRAS, JL ;
CHANG, YYKW ;
BERTRAND, M .
TETRAHEDRON LETTERS, 1982, 23 (35) :3571-3572
[8]   Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions [J].
Groaning, MD ;
Meyers, AI .
TETRAHEDRON, 2000, 56 (51) :9843-9873
[9]   Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives:: Synthesis of the antibiotic CJ-15,801 [J].
Han, C ;
Shen, RC ;
Su, S ;
Porco, JA .
ORGANIC LETTERS, 2004, 6 (01) :27-30
[10]   STEREOCHEMISTRY AND ABSOLUTE CONFIGURATION OF STENINE AND TUBEROSTEMONINE [J].
HARADA, H ;
IRIE, H ;
MASAKI, N ;
OSAKI, K ;
UYEO, S .
CHEMICAL COMMUNICATIONS, 1967, (09) :460-&