Kinetically controlled cross-metathesis reactions with high E-olefin selectivities

被引:53
作者
Engelhardt, FC [1 ]
Schmitt, MJ [1 ]
Taylor, RE [1 ]
机构
[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA
关键词
D O I
10.1021/ol016061z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Homoallylic alcohols with anti-allylic substituents display enhanced E-olefin selectivity in cross-metathesis (CM) reactions with allyltrimethylsilane. The high selectivity can be explained via a five membered chelate intermediate in which the hydroxyl group of the homoallylic alcohol coordinates to the ruthenium metal center of Grubbs' catalyst.
引用
收藏
页码:2209 / 2212
页数:4
相关论文
共 21 条
[1]   New approaches to olefin cross-metathesis [J].
Blackwell, HE ;
O'Leary, DJ ;
Chatterjee, AK ;
Washenfelder, RA ;
Bussmann, DA ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) :58-71
[2]   Synthesis of trisubstituted alkenes via olefin cross-metathesis [J].
Chatterjee, AK ;
Grubbs, RH .
ORGANIC LETTERS, 1999, 1 (11) :1751-1753
[3]  
Choi TL, 2001, ANGEW CHEM INT EDIT, V40, P1277, DOI 10.1002/1521-3773(20010401)40:7<1277::AID-ANIE1277>3.3.CO
[4]  
2-5
[5]   Preparation of allylsilanes via cross-metathesis [J].
Crowe, WE ;
Goldberg, DR ;
Zhang, ZJ .
TETRAHEDRON LETTERS, 1996, 37 (13) :2117-2120
[6]   Well-defined ruthenium olefin metathesis catalysts: Mechanism and activity [J].
Dias, EL ;
Nguyen, ST ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) :3887-3897
[7]  
Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
[8]   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
[9]   Exploiting the reversibility of olefin metathesis.: Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin [J].
Fürstner, A ;
Thiel, OR ;
Ackermann, L .
ORGANIC LETTERS, 2001, 3 (03) :449-451
[10]   Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].
Garber, SB ;
Kingsbury, JS ;
Gray, BL ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179