Ruthenium-catalyzed [2+2] cycloadditions of ynamides

被引:98
作者
Riddell, N [1 ]
Villeneuve, K
Tam, W
机构
[1] Univ Guelph, Guelph Waterloo Ctr Grad Work Chem, Guelph, ON N1G 2W1, Canada
[2] Univ Guelph, Dept Biochem & Chem, Guelph, ON N1G 2W1, Canada
关键词
D O I
10.1021/ol0512841
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Ruthenium-catalyzed [2 + 2] cycloadditions between norbornene and ynamides were investigated. The ynamide moiety was found to be compatible with the ruthenium-catalyzed cycloaddition conditions, giving the corresponding cyclobutene cycloadducts in moderate to good yields (up to 97%).
引用
收藏
页码:3681 / 3684
页数:4
相关论文
共 80 条
[1]   Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].
Brummond, KM ;
Kent, JL .
TETRAHEDRON, 2000, 56 (21) :3263-3283
[2]  
Buchwald S. L., 1999, COMPREHENSIVE ASYMME, V2, P491
[3]   Cross [2+2] cycloaddition of bicyclic alkenes with alkynes mediated by cobalt complexes: A facile synthesis of cyclobutene derivatives [J].
Chao, KC ;
Rayabarapu, DK ;
Wang, CC ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :8804-8810
[4]  
Chung YK, 1999, COORDIN CHEM REV, V188, P297
[5]   Palladium-catalyzed Suzuki-Miyaura coupling reactions involving β,β-dihaloenamides:: Application to the synthesis of disubstituted ynamides [J].
Couty, S ;
Barbazanges, M ;
Meyer, C ;
Cossy, J .
SYNLETT, 2005, (06) :905-910
[6]   Heck-Suzuki-Miyaura domino reactions involving ynamides.: An efficient access to 3-(Arylmethylene)isoindolinones [J].
Couty, S ;
Liégault, B ;
Meyer, C ;
Cossy, J .
ORGANIC LETTERS, 2004, 6 (15) :2511-2514
[7]   Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides [J].
Dunetz, JR ;
Danheiser, RL .
ORGANIC LETTERS, 2003, 5 (21) :4011-4014
[8]   YNAMINE - VERSATILE TOOL IN ORGANIC-SYNTHESIS [J].
FICINI, J .
TETRAHEDRON, 1976, 32 (13) :1449-1486
[9]   Highly stereoselective Saucy-Marbet rearrangement using chiral ynamides. Synthesis of highly substituted chiral homoallenyl alcohols [J].
Frederick, MO ;
Hsung, RP ;
Lambeth, RH ;
Mulder, JA ;
Tracey, MR .
ORGANIC LETTERS, 2003, 5 (15) :2663-2666
[10]   A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides [J].
Frederick, MO ;
Mulder, JA ;
Tracey, MR ;
Hsung, RP ;
Huang, J ;
Kurtz, KCM ;
Shen, LC ;
Douglas, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2368-2369