Preparative-Scale Synthesis of Vedejs']js Chiral DMAP Catalysts

被引：9

作者：

Kinens, Artis ^{[1
,2
]}

Balkaitis, Simonas ^{[1
,2
]}

Suna, Edgars ^{[1
,2
]}

机构：

[1] Latvian Inst Organ Synth, Aizkraukles 21, LV-1006 Riga, Latvia

[2] Univ Latvia, Dept Chem, Jelgavas 1, LV-1004 Riga, Latvia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 20期

关键词：

KINETIC RESOLUTION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC ACYLATION; SEC-ALCOHOLS; DERIVATIVES; 4-(DIMETHYLAMINO)PYRIDINE; LITHIATION; COMPLEXES; AMINATION; AROMATICS;

D O I：

10.1021/acs.joc.8b01687

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A scalable synthesis of chiral Vedejs-type DMAP catalysts is reported. The key step of the synthesis is amination of the enantiomerically pure 4-chloropyridine derivative using well-defined ZnCl2(amine)(2) complexes. A series of Zn(II)-amine complexes have been synthesized to explore the scope of the ZnCl2-mediated amination of 4-halopyridines. Mechanistic studies support a Zn(II)-facilitated nucleophilic aromatic substitution as a plausible mechanism for the chlorine-to-amine exchange.

引用

页码：12449 / 12459

页数：11

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