ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE PYRIDINE-DERIVATIVES AND C-2-SYMMETRICAL 2,2'-BIPYRIDINES

被引：218

作者：

BOLM, C

EWALD, M

FELDER, M

SCHLINGLOFF, G

机构：

[1] Institut für Organische Chemie der, Universität Basel, Basel, CH-4056

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 05期

关键词：

2,2'-BIPYRIDINES; PYRIDINES; OPTICALLY ACTIVE; CHIRAL LIGANDS; ASYMMETRIC SYNTHESIS; CATALYSIS; ENANTIOSELECTIVE;

D O I：

10.1002/cber.19921250528

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active pyridine derivatives 2, 15, 18, 19, 21, 26, and 27 are obtained by enantioselective reduction of the corresponding ketones 5, 7, 11-13, 24, and 25 using the chiral borane reagent chlorodiisopinocampheylborane [(Ipc)2BCl]. Nickel(0)-mediated coupling of bromopyridines 2, 15, and 31 gives C2-symmetric 2,2'-bipyridines (RR)-32, (RR)-33, and (SS)-38, respectively, which form metal complexes with Co(II), Pd(II), Cu(I), and Ag(I). Aryl-substituted pyridines 26, and 39-41 are synthesized by palladium(0)-catalyzed cross couplings of 2 and 15 with boronic acids 42-44.

引用

页码：1169 / 1190

页数：22

共 95 条

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