Chemoenzymatic synthesis of chiral 2,2′-bipyridine ligands and their N-oxide derivatives: applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes

被引：31

作者：

Boyd, D. R. ^{[1
]}

Sharma, N. D. ^{[1
]}

Sbircea, L. ^{[1
]}

Murphy, D. ^{[1
]}

Malone, J. F. ^{[1
]}

James, S. L. ^{[1
]}

Allen, C. C. R. ^{[2
]}

Hamilton, J. T. G. ^{[3
]}

机构：

[1] Queens Univ Belfast, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland

[2] Queens Univ Belfast, Sch Biol Sci, Belfast BT9 5AG, Antrim, North Ireland

[3] Inst No Ireland, Belfast BT9 5PX, Antrim, North Ireland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 05期

基金：

爱尔兰科学基金会;

关键词：

ENANTIOSELECTIVE ALLYLATION; BIPYRIDINE N; N'-DIOXIDES; DIOXYGENASE; DIHYDROXYLATION; ORGANOCATALYSTS; PHENOL; AMINES;

D O I：

10.1039/b919894f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of enantiopure 2,2'-bipyridines have been synthesised from the corresponding cis-dihydrodiol metabolites of 2-chloroquinolines. Several of the resulting hydroxylated 2,2'-bipyridines were found to be useful chiral ligands for the asymmetric aminolysis of meso-epoxides leading to the formation of enantioenriched amino alcohols (-> 84%ee). N-oxide and N,N'-dioxide derivatives of these 2,2'-bipyridines, including separable atropisomers, have been synthesised and used as enantioselective organocatalysts in the asymmetric allylation of aldehydes to give allylic alcohols (-> 86%ee).

引用

页码：1081 / 1090

页数：10