Group-selective ring-closing enyne metathesis: Concentration-dependent selectivity profile of alkynylsilyloxy-tethered dienynes

被引:34
作者
Maifeld, SV [1 ]
Miller, RL [1 ]
Lee, D [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
关键词
D O I
10.1021/ja046043n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly group-selective ring-closing metathesis of alkynylsilyloxy-tethered dienynes was achieved by using Grubbs first- and second-generation catalyst. The remarkable selectivity increase at higher concentration for differentiating between two alkene moieties in nearly identical steric and stereoelectronic environments is believed to be the result of a higher ring-closure rate for smaller-sized ring formation under rapid pre-equilibration of the two alkylidene species generated from either alkene moiety. Copyright © 2004 American Chemical Society.
引用
收藏
页码:12228 / 12229
页数:2
相关论文
共 29 条
[1]  
[Anonymous], 2003, HDB METATHESIS
[2]   Asymmetric allylboration and ring closing alkene metathesis: A novel strategy for the synthesis of glycosphingolipids [J].
Barrett, AGM ;
Beall, JC ;
Braddock, DC ;
Flack, K ;
Gibson, VC ;
Salter, MM .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6508-6514
[3]  
BOIS M, 1995, CHEM REV, V95, P1253
[4]   Recent developments in olefin cross-metathesis [J].
Connon, SJ ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923
[5]   Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].
Deiters, A ;
Martin, SF .
CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238
[6]   Enyne metathesis (enyne bond reorganization) [J].
Diver, ST ;
Giessert, AJ .
CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382
[7]   Diastereoselective temporary silicon-tethered ring-closing-metathesis reactions with prochiral alcohols: A new approach to long-range asymmetric induction [J].
Evans, PA ;
Cui, B ;
Buffone, GP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1734-1737
[8]   Temporary silicon-tethered ring-closing metathesis approach to C2-symmetrical 1,4-diols:: Asymmetric synthesis of D-altritol [J].
Evans, PA ;
Murthy, VS .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6768-6769
[9]  
Fensterbank L, 1997, SYNTHESIS-STUTTGART, P813
[10]   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