Group-selective ring-closing enyne metathesis

被引:65
作者
Maifeld, SV [1 ]
Lee, D [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
关键词
cyclization; enynes; metathesis; ruthenium;
D O I
10.1002/chem.200500407
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The ring-closing metathesis (RCM) of dienynes represents a powerful methodology for the construction of mono- and bicyclic systems containing 1,3-diene functionality. Despite its synthetic potential, the utility of dienyne RCM is significantly reduced due to poor group selectivity. To circumvent this shortcoming, several strategies utilizing steric hindrance, electronic variation, relay metathesis and ring-closure kinetics have been implemented to exert control over the reaction pathways. Ibis article highlights a variety of methods to achieve group-selective enyne RCM of dienynes.
引用
收藏
页码:6118 / 6126
页数:9
相关论文
共 57 条
[1]  
[Anonymous], 2003, HDB METATHESIS
[2]   Formal synthesis of (±)-guanacastepene A:: A tandem ring-closing metathesis approach [J].
Boyer, FD ;
Hanna, I ;
Ricard, L .
ORGANIC LETTERS, 2004, 6 (11) :1817-1820
[3]   Synthesis of polyoxygenated bicyclic systems containing medium-sized rings from carbohydrates via tandem metathesis of dienynes [J].
Boyer, FD ;
Hanna, I ;
Ricard, L .
ORGANIC LETTERS, 2001, 3 (20) :3095-3098
[4]   Synthesis of functionalized olefins by cross and ring-closing metatheses [J].
Chatterjee, AK ;
Morgan, JP ;
Scholl, M ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784
[5]   Tandem ring-closing metathesis reaction with a ruthenium catalyst containing a N-heterocyclic ligand [J].
Choi, TL ;
Grubbs, RH .
CHEMICAL COMMUNICATIONS, 2001, (24) :2648-2649
[6]  
Connon S. J, 2003, Angew. Chem, V115, P1944
[7]   Recent developments in olefin cross-metathesis [J].
Connon, SJ ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923
[8]   SUBSTRATE-CONTROLLED GROUP-SELECTIVE RADICAL CYCLIZATIONS - A NEW STRATEGY FOR STEREOCONTROLLED TRANSFORMATIONS OF DIASTEREOMERIC REACTIVE INTERMEDIATES [J].
CURRAN, DP ;
QI, HY ;
DEMELLO, NC ;
LIN, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :8430-8431
[9]   Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].
Deiters, A ;
Martin, SF .
CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238
[10]   Enyne metathesis (enyne bond reorganization) [J].
Diver, ST ;
Giessert, AJ .
CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382