Synthesis of eight-membered ring compounds using enyne metathesis

被引:83
作者
Mori, M [1 ]
Kitamura, T [1 ]
Sakakibara, N [1 ]
Sato, Y [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
D O I
10.1021/ol991398a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel procedure for synthesizing eight-membered ring compounds was developed using ruthenium-catalyzed enyne metathesis. When a CH2Cl2 solution Of enyne connected with catechol, o-amino phenol, or o-phenylenediamine was stirred in the presence of benzylidene ruthenium carbene complex (10 mol %) at room temperature overnight, an eight-membered ring compound was obtained in high yield. In a similar manner, monocyclic 1,4-diaza or 1-oxa-4-azacyclooctene derivative was obtained in high yield.
引用
收藏
页码:543 / 545
页数:3
相关论文
共 17 条
[1]   Enyne metathesis for the facile synthesis of highly functionalised novel bicyclic beta-lactams [J].
Barrett, AGM ;
Baugh, SPD ;
Braddock, DC ;
Flack, K ;
Gibson, VC ;
Procopiou, PA .
CHEMICAL COMMUNICATIONS, 1997, (15) :1375-1376
[2]   HIGHLY SELECTIVE SKELETAL REORGANIZATION OF 1,6-ENYNE AND 1,7-ENYNE TO 1-VINYLCYCLOALKENES CATALYZED BY [RUCL2(CO)(3)](2) [J].
CHATANI, N ;
MORIMOTO, T ;
MUTO, T ;
MURAI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6049-6050
[3]   THE APPLICATION OF CATALYTIC RING-CLOSING OLEFIN METATHESIS TO THE SYNTHESIS OF UNSATURATED OXYGEN HETEROCYCLES [J].
FU, GC ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5426-5427
[4]  
Fürstner A, 1998, TOP ORGANOMETAL CHEM, V1, P37
[5]   An enyne metathesis/(4+2)-dimerization route to (±)-differolide [J].
Hoye, TR ;
Donaldson, SM ;
Vos, TJ .
ORGANIC LETTERS, 1999, 1 (02) :277-279
[6]   METAL-CATALYZED REARRANGEMENT OF ALKENE ALKYNES AND THE STEREOCHEMISTRY OF METALLACYCLOBUTENE RING-OPENING [J].
KATZ, TJ ;
SIVAVEC, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (03) :737-738
[7]   CATALYTIC RING CLOSING METATHESIS OF DIENYNES - CONSTRUCTION OF FUSED BICYCLIC RINGS [J].
KIM, SH ;
BOWDEN, N ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10801-10802
[8]   Catalytic ring closing metathesis of dienynes: Construction of fused bicyclic [nm0] rings [J].
Kim, SH ;
Zuercher, WJ ;
Bowden, NB ;
Grubbs, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :1073-1081
[9]  
Kinoshita A, 1997, HETEROCYCLES, V46, P287
[10]   Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis [J].
Kinoshita, A ;
Sakakibara, N ;
Mori, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12388-12389