Expanded scope in ethylene-alkyne cross-metathesis: Coordinating heteroatom functionality at the propargylic position

被引:105
作者
Smulik, JA [1 ]
Diver, ST [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1021/ol006035l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The Grubbs 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene-substituted ruthenium complex 1 catalyzed ethylene-alkyne cross-metathesis and was shown to tolerate free hydroxyl groups and coordinating functionality at the propargylic and homopropargylic positions, Hindered and enantiomerically enriched 1-substituted alkynes also react efficiently under the reported conditions.
引用
收藏
页码:2271 / 2274
页数:4
相关论文
共 19 条
[1]  
DIVER ST, UNPUB
[2]   CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX [J].
FU, GC ;
NGUYEN, ST ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9856-9857
[3]   SYNTHESIS OF NITROGEN-HETEROCYCLES VIA CATALYTIC RING-CLOSING METATHESIS OF DIENES [J].
FU, GC ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7324-7325
[4]   Ruthenium carbene complexes with N,N′-bis(mesityl) imidazol-2-ylidene ligands:: RCM catalysts of extended scope [J].
Fürstner, A ;
Thiel, OR ;
Ackermann, L ;
Schanz, HJ ;
Nolan, SP .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :2204-2207
[5]   Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond formations [J].
Furstner, A ;
Langemann, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) :9130-9136
[6]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[7]   RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].
GRUBBS, RH ;
MILLER, SJ ;
FU, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452
[8]   Total synthesis of (-)-stemoamide using ruthenium-catalyzed enyne metathesis reaction [J].
Kinoshita, A ;
Mori, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8356-8357
[9]   Remarkable effect of ethylene gas in the intramolecular enyne metathesis of terminal alkynes [J].
Mori, M ;
Sakakibara, N ;
Kinoshita, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6082-6083
[10]   SYNTHESES AND ACTIVITIES OF NEW SINGLE-COMPONENT, RUTHENIUM-BASED OLEFIN METATHESIS CATALYSTS [J].
NGUYEN, ST ;
GRUBBS, RH ;
ZILLER, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9858-9859