Effects of olefin substitution on the ring-closing metathesis of dienes

被引:258
作者
Kirkland, TA [1 ]
Grubbs, RH [1 ]
机构
[1] CALTECH,ARNOLD & MABEL BECKMAN LABS CHEM SYNTHESIS,DIV CHEM & CHEM ENGN,PASADENA,CA 91125
关键词
D O I
10.1021/jo970877p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ruthenium alkylidene 1 and molybdenum alkylidene 2 have been utilized in the ring-closing metathesis (RCM) of dienes containing gem-disubstituted olefins to yield td-and tetrasubstituted cyclic olefins. Dienes with sterically demanding and/or electron-withdrawing substituents such as Ph, CO2Me, and Bu-t were cyclized successfully with 2, but did not cyclize with 1. Tetrasubstituted cyclic olefins could be formed with 2, but not using alkylidene-1. Dienes with allylic functional groups yielded functionalized cyclic olefins when treated with 1.
引用
收藏
页码:7310 / 7318
页数:9
相关论文
共 50 条
[1]   BIOSYNTHESIS OF TERPENES AND STEROIDS .5. SYNTHESIS OF ERGOSTA-5,7,22,24(28)-TETRAEN-3BETA-OL, A BIOSYNTHETIC PRECURSOR OF ERGOSTEROL [J].
BARTON, DHR ;
SHIORI, T ;
WIDDOWSON, DA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (10) :1968-+
[2]   SYNTHETICAL STUDIES OF TERPENOIDS .13. SYNTHESES OF MODEL COMPOUNDS RELATED TO XANTHATIN [J].
BHANOT, OS ;
DUTTA, PC .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (20) :2583-+
[3]   THE FIRST SYNTHESIS OF THE ABCD RING-SYSTEM OF MANZAMINE-A - CONSTRUCTION OF THE MACROCYCLIC RING-D [J].
BORER, BC ;
DEERENBERG, S ;
BIERAUGEL, H ;
PANDIT, UK .
TETRAHEDRON LETTERS, 1994, 35 (19) :3191-3194
[4]   ARENE IMINIUM SALT ELECTRON-TRANSFER PHOTOCHEMISTRY - MECHANISTICALLY INTERESTING PHOTOADDITION PROCESSES [J].
BORG, RM ;
HEUCKEROTH, RO ;
LAN, AJY ;
QUILLEN, SL ;
MARIANO, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2728-2737
[5]   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
[6]  
Clark JS, 1997, TETRAHEDRON LETT, V38, P127
[7]  
Clark JS, 1997, TETRAHEDRON LETT, V38, P123
[8]   Some barbituric acids containing the 2-methylallyl group [J].
Doran, WJ ;
Shonle, HA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :1625-1626
[9]   SOLVENT-FREE CYCLIZATION OF LINEAR DIENES USING OLEFIN METATHESIS AND THE THORPE INGOLD EFFECT [J].
FORBES, MDE ;
PATTON, JT ;
MYERS, TL ;
MAYNARD, HD ;
SMITH, DW ;
SCHULZ, GR ;
WAGENER, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10978-10980
[10]  
FRANK RL, 1955, ORG SYNTH, V3, P499