Kumada-Corriu coupling of Grignard reagents, probed with a chiral Grignard reagent

被引:74
作者
Hölzer, B [1 ]
Hoffmann, RW [1 ]
机构
[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
关键词
D O I
10.1039/b300033h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Grignard reagent 2, in which the magnesium-bearing carbon atom is the sole stereogenic centre has been coupled with vinyl bromide under Pd(0) or Ni(0)-catalysis to give compound 3 with full retention of configuration. Coupling using Fe(acac)(3) or Co(acac)(2) as catalyst was accompanied by considerable racemisation. These findings are discussed with respect to a dichotomy between concerted polar and stepwise SET transmetallation pathways.
引用
收藏
页码:732 / 733
页数:2
相关论文
共 34 条
[1]  
Boudier A, 2000, CHEM-EUR J, V6, P2748, DOI 10.1002/1521-3765(20000804)6:15<2748::AID-CHEM2748>3.0.CO
[2]  
2-Q
[3]  
Boudier A, 2000, ANGEW CHEM INT EDIT, V39, P2294, DOI 10.1002/1521-3773(20000703)39:13<2294::AID-ANIE2294>3.3.CO
[4]  
2-A
[5]  
Boudier A., 2000, ANGEW CHEM, V112, P2396
[6]   Cobalt-catalyzed alkenylation of organomagnesium reagents [J].
Cahiez, G ;
Avedissian, H .
TETRAHEDRON LETTERS, 1998, 39 (34) :6159-6162
[7]   STEREOSELECTIVE FORMATION OF C-C BOND IN COUPLING REACTION BETWEEN SECONDARY ALKYLMAGNESIUM BROMIDES AND UNSATURATED HALIDES - ASYMMETRICAL INDUCTION BY OPTICALLY-ACTIVE DIPHOSPHINE NICKEL-COMPLEX [J].
CONSIGLIO, G ;
BOTTEGHI, C .
HELVETICA CHIMICA ACTA, 1973, 56 (01) :460-463
[8]  
Corriu R.J. P., 1972, J CHEM SOC CHEM COMM, P144
[9]   UNPRECEDENTED AND REVERSIBLE COBALT-TO-CARBON ALKYL BOND REARRANGEMENT IN THE COENZYME-B12 MODEL COMPLEX C6H5CH2COIII[C2(DO)(DOH)PN]I - SYNTHESIS, STRUCTURAL CHARACTERIZATION, AND MECHANISTIC STUDIES [J].
DAIKH, BE ;
FINKE, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4160-4172
[10]   THE PERSISTENT RADICAL EFFECT - A PROTOTYPE EXAMPLE OF EXTREME, 10(5) TO 1, PRODUCT SELECTIVITY IN A FREE-RADICAL REACTION INVOLVING PERSISTENT BULLET-CO(II)[MACROCYCLE] AND ALKYL FREE-RADICALS [J].
DAIKH, BE ;
FINKE, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :2938-2943