Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation

被引：56

作者：

Rueping, Magnus ^{[1
]}

Stoeckel, Mirjam ^{[2
]}

Sugiono, Erli ^{[1
]}

Theissmann, Thomas ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

[2] Sanofi Aventis Deutschland GmbH, D-60444 Frankfurt, Germany

来源：

TETRAHEDRON | 2010年 / 66卷 / 33期

关键词：

Flumequine; Levofloxacine; Bronsted acid; Asymmetric reduction; Organocatalysis; ALPHA-IMINO ESTERS; ENANTIOSELECTIVE TRANSFER HYDROGENATION; CATALYZED TRANSFER HYDROGENATION; CHIRAL PHOSPHORIC-ACIDS; ANTIBACTERIAL ACTIVITIES; ABSOLUTE-CONFIGURATION; KEY INTERMEDIATE; REDUCTION; LEVOFLOXACIN; EFFICIENT;

D O I：

10.1016/j.tet.2010.04.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantioselective organocatalytic transfer hydrogenation enabling the synthesis of both 6-fluoro-2-methyltetrahydroquinoline and 7,8-difluoro-3-methyl-benzoxazine has been developed. These key building blocks can for the first time be synthesized using the same methodology allowing fast and efficient, metal-free access to the antibiotic fluoroquinolones flumequine and levofloxacine. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6565 / 6568

页数：4

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