One-pot enantioselective formation of eight-membered rings from alkenyl Fischer carbene complexes and ketone enolates

被引:29
作者
Barluenga, J [1 ]
Diéguez, A [1 ]
Rodríguez, F [1 ]
Flórez, J [1 ]
Fañanás, FJ [1 ]
机构
[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada CSIC, E-33071 Oviedo, Spain
关键词
D O I
10.1021/ja0264551
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Eight-membered carbocycles with up to five new stereogenic centers are enantioselectively obtained following a one-pot procedure that involves the coupling of three components: an alkenyl Fischer carbene complex, a ketone enolate, and allyl lithium. Copyright © 2002 American Chemical Society.
引用
收藏
页码:9056 / 9057
页数:2
相关论文
共 28 条
[1]   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
[2]  
Barluenga J, 2000, ANGEW CHEM INT EDIT, V39, P4346, DOI 10.1002/1521-3773(20001201)39:23<4346::AID-ANIE4346>3.0.CO
[3]  
2-8
[4]   Unusual [1,2]- and [1,3]-M(CO)5 shifts in Fischer carbene complexes:: [4+3] and [3+3] annulation reactions of furan and pyrrole rings [J].
Barluenga, J ;
Tomás, M ;
Rubio, E ;
López-Pelegrín, JA ;
García-Granda, S ;
Priede, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3065-3071
[5]  
Barluenga J, 2000, ANGEW CHEM INT EDIT, V39, P2460
[6]   Intramolecular C-H insertion reactions of boroxy Fischer carbene complexes.: Regio- and diastereoselective modification of terpenes [J].
Barluenga, J ;
Rodríguez, F ;
Vadecard, J ;
Bendix, M ;
Fañanás, FJ ;
López-Ortiz, F ;
Rodríguez, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (38) :8776-8782
[7]  
BARLUENGA J, 1994, ANGEW CHEM INT EDIT, V33, P1392, DOI 10.1002/anie.199413921
[8]   STEREOSELECTIVE SYNTHESIS OF 7-MEMBERED CARBOCYCLES FROM 2-AMINO-1,3-BUTADIENES AND VINYL CHROMIUM FISCHER-TYPE CARBENES [J].
BARLUENGA, J ;
AZNAR, F ;
MARTIN, A ;
VAZQUEZ, JT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (37) :9419-9426
[9]   Intramolecular C-H insertion reactions of boroxy Fischer carbene complexes [J].
Barluenga, J ;
Rodriguez, F ;
Vadecard, J ;
Bendix, M ;
Fananas, FJ ;
LopezOrtiz, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) :6090-6091
[10]   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