Formal alkyne insertion into alkoxycarbene complexes:: Simple access to enantiopure group 6 alkynyl(alkoxy)carbene complexes

被引:39
作者
Barluenga, J [1 ]
de la Rúa, RB [1 ]
de Sáa, D [1 ]
Ballesteros, A [1 ]
Tomás, M [1 ]
机构
[1] Univ Oviedo, CSIC, Inst Quim, Unidad Associada, E-33006 Oviedo, Spain
关键词
acetylides; asymmetric synthesis; carbene complexes; cycloaddition; rearrangements;
D O I
10.1002/anie.200501400
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A single (or iterative) insertion of alkyne units into metal carbene complexes, accompanied by alkoxy exchange, occurs readily to give elusive alkynyl-(alkoxy)carbenes (see scheme) as well as polyalkynyl(alkoxy)carbenes. M = W, Cr, Mo. TMSOTf = trimethylsilyl trifluoromethanesulfonate. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4981 / 4983
页数:3
相关论文
共 36 条
[11]  
de Meijere A, 2000, ANGEW CHEM INT EDIT, V39, P3964, DOI 10.1002/1521-3773(20001117)39:22<3964::AID-ANIE3964>3.0.CO
[12]  
2-C
[13]  
DORWAL FZ, 1999, METAL CARBENES ORGAN
[14]   REACTIONS OF COMPLEX LIGANDS .65. VINYLIDENE AND METHOXY(ALKYNYL)CARBENE MOLYBDENUM COMPLEXES - COMPETITIVE FORMATION DURING FISCHER CARBENE COMPLEX SYNTHESIS AND CRYSTAL-STRUCTURE DETERMINATION [J].
DOTZ, KH ;
CHRISTOFFERS, C ;
CHRISTOFFERS, J ;
BOTTCHER, D ;
NIEGER, M ;
KOTILA, S .
CHEMISCHE BERICHTE, 1995, 128 (06) :645-648
[15]  
Fischer E.O., 1964, ANGEW CHEM, V76, P645
[16]   Synthetic routes to transition-metal-substituted pentadiynylidene complexes [J].
Hartbaum, C ;
Fischer, H .
CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (08) :1063-1067
[17]  
HIETBRINK BN, 2001, 221 ACS NAT M SAN DI
[18]   First enantioselective catalytic Diels-Alder reaction of dienes and acetylenic aldehydes: Experimental and theoretical evidence for the predominance of exo-transition structure [J].
Ishihara, K ;
Kondo, S ;
Kurihara, H ;
Yamamoto, H ;
Ohashi, S ;
Inagaki, S .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3026-3027
[19]   The asymmetric [3+2] cycloaddition reaction of chiral alkenyl Fischer carbene complexes with imines: Synthesis of optically pure 2,5-disubstituted-3-pyrrolidinones [J].
Kagoshima, H ;
Okamura, T ;
Akiyama, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (29) :7182-7183
[20]   Michael addition of chiral Fischer aminocarbene complexes to nitroolefins: Study on the effect of the Michael acceptor structure on diastereoselectivity [J].
Licandro, E ;
Maiorana, S ;
Capella, L ;
Manzotti, R ;
Papagni, A ;
Vandoni, B ;
Albinati, A ;
Chuang, SH ;
Hwu, JR .
ORGANOMETALLICS, 2001, 20 (03) :485-496