Cyclopropanation of alkenes mediated by novel chiral Fischer carbene complexes

被引:8
作者
Barluenga, J [1 ]
Muñiz, K [1 ]
Ballesteros, A [1 ]
Martínez, S [1 ]
Tomás, M [1 ]
机构
[1] Univ Oviedo, Inst Univ Quim Organomet E Moles, Julian Claveria 8, E-33006 Oviedo, Spain
关键词
cyclopropanation; alkenes; chiral Fischer carbene complexes; group; 6; diastereoselective; enantioselective;
D O I
10.3998/ark.5550190.0003.513
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclopropanation reaction using chiral-at-metal Fischer carbene complexes is examined. Racemic molybdenum and chromium carbene complexes fac- and mer-1 and mer-2, respectively, undergo cycloaddition to acrylonitrile, methyl acrylate and 1-hexene to give cylopropanes 3 and 4 with trans/cis ratio up to 4.7:1. The cyclopropanation of acrylonitrile with the enantiopure carbene complex (+)-mer-1 resulted in a modest asymmetric induction of 2: 1 for the transisomer 3a.
引用
收藏
页码:110 / 119
页数:10
相关论文
共 61 条
[1]  
ARATANI T, 2000, CONT ASYMMETRIC CATA, V1
[2]   TRICYCLIC ETHERS FROM FISCHER VINYLCARBENE COMPLEXES AND BETA-OXYGEN-FUNCTIONALIZED ORGANOLITHIUM COMPOUNDS [J].
BARLUENGA, J ;
MONTSERRAT, JM ;
FLOREZ, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (13) :1068-1070
[3]  
Barluenga J, 2001, ANGEW CHEM INT EDIT, V40, P3392, DOI 10.1002/1521-3773(20010917)40:18<3392::AID-ANIE3392>3.0.CO
[4]  
2-Y
[5]   STEREOSELECTIVE CYCLOPROPANATION OF 1-AZADIENES WITH FISCHER CARBENE COMPLEXES [J].
BARLUENGA, J ;
TOMAS, M ;
LOPEZPELEGRIN, JA ;
RUBIO, E .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (06) :665-666
[6]   Diastereoselective intermolecular cyclopropanation of simple alkenes by fischer alkenyl and heteroaryl carbene complexes of chromium:: Scope and limitations [J].
Barluenga, J ;
López, S ;
Trabanco, AA ;
Fernández-Acebes, A ;
Flórez, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8145-8154
[7]  
BARLUENGA J, UNPUB
[8]   CYCLOPROPANES FROM REACTIONS OF TRANSITION-METAL CARBENE COMPLEXES WITH OLEFINS [J].
BROOKHART, M ;
STUDABAKER, WB .
CHEMICAL REVIEWS, 1987, 87 (02) :411-432
[9]   REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANE DERIVATIVES FROM 1,3-DIENES AND A FISCHER CARBENE COMPLEX [J].
BUCHERT, M ;
REISSIG, HU .
TETRAHEDRON LETTERS, 1988, 29 (19) :2319-2320
[10]   ON THE REGIOSELECTIVITY AND STEREOSELECTIVITY OF THE CARBENE TRANSFER FROM FISCHER CARBENE COMPLEXES TO TRISUBSTITUTED ELECTRON-DEFICIENT 1,3-DIENES [J].
BUCHERT, M ;
HOFFMANN, M ;
REISSIQ, HU .
CHEMISCHE BERICHTE, 1995, 128 (06) :605-614