Rhodium(I)-catalyzed [3+2+2]-cyclization of alkenyl Fischer carbene complexes with methyl buta-2,3-dienoate

被引:14
作者
Barluenga, Jose [1 ]
Vicente, Ruben [1 ]
Lopez, Luis A. [1 ]
Tomas, Miguel [1 ]
机构
[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, Unidad Asociada CSIC, E-33071 Oviedo, Spain
关键词
Fischer carbenes; Rhodium(I) carbenes; Allenes; Cycloaddition; Carbene transfer; TRANSITION-METAL-COMPLEXES; ORGANIC SYNTHESES; REACTIVITY ENHANCEMENT; CHEMICAL MULTITALENTS; CHIRAL BUTADIENES; 3+2 CYCLIZATION; IRON COMPLEXES; CHROMIUM; RHODIUM; METHYLENATION;
D O I
10.1016/j.tet.2010.04.130
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of alkenyl chromium Fischer carbene complexes react with methyl buta-2,3-dienoate in the presence of a rhodium catalyst to afford substituted cycloheptene derivatives 7, along with minor amounts of cyclopentene derivatives 6. Through this [3+2+2]-cyclization two allene units and one alkenyl carbene ligand are assembled in a selective manner. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6335 / 6339
页数:5
相关论文
共 45 条
[1]  
Albéniz AC, 2002, ANGEW CHEM INT EDIT, V41, P2363, DOI 10.1002/1521-3773(20020703)41:13<2363::AID-ANIE2363>3.0.CO
[2]  
2-9
[3]   ORGANIC SYNTHESES WITH TRANSITION-METAL COMPLEXES .30. TRIMETHYLENEMETHANE IRON COMPLEXES VIA METHYLENATION OF ALLENES WITH CARBENE IRON COMPLEXES [J].
AUMANN, R ;
MELCHERS, HD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 355 (1-3) :351-358
[4]  
Aumann R, 1999, EUR J ORG CHEM, V1999, P2545
[5]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .36. MONOFUNCTIONAL TRI(METHYLENE)METHANE CHROMIUM AND IRON COMPLEXES BY ADDITION OF ALLENES TO M = C BONDS OF CARBENE COMPLEXES [J].
AUMANN, R ;
TRENTMANN, B .
CHEMISCHE BERICHTE-RECUEIL, 1989, 122 (10) :1977-1982
[7]   Group 6 Fischer carbene complexes:: "chemical multitalents" for multi-component reactions [J].
Barluenga, J ;
Fernández-Rodríguez, MA ;
Aguilar, E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (03) :539-587
[8]   Specific synthesis of 1,2- and 1,3-dialkylidenecycloheptanes by [3+2+2] cyclization of alkenyl Fischer carbene complexes and allenes [J].
Barluenga, J ;
Vicente, R ;
Barrio, P ;
López, LA ;
Tomás, M ;
Borge, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (44) :14354-14355
[9]   Metal-controlled selective [3+2] cyclization reactions of alkenyl Fischer carbene complexes and allenes [J].
Barluenga, J ;
Vicente, R ;
Barrio, P ;
López, LA ;
Tomás, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5974-5975
[10]   Synthesis of heterocycles via group VI Fischer carbene complexes [J].
Barluenga, J ;
Santamaría, J ;
Tomás, M .
CHEMICAL REVIEWS, 2004, 104 (05) :2259-2283