Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation

Magnus Rueping; Mirjam Stoeckel; Erli Sugiono; Thomas Theissmann

doi:10.1016/j.tet.2010.04.091

Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation

Magnus Rueping^*, Mirjam Stoeckel, Erli Sugiono, Thomas Theissmann

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	6565-6568
Number of pages	4
Journal	Tetrahedron
Volume	66
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2010.04.091
State	Published - Aug 14 2010
Externally published	Yes

Keywords

Asymmetric reduction
Brønsted acid
Flumequine
Levofloxacine
Organocatalysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2010.04.091

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title = "Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation",

abstract = "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.",

keywords = "Asymmetric reduction, Br{\o}nsted acid, Flumequine, Levofloxacine, Organocatalysis",

author = "Magnus Rueping and Mirjam Stoeckel and Erli Sugiono and Thomas Theissmann",

year = "2010",

month = aug,

day = "14",

doi = "10.1016/j.tet.2010.04.091",

language = "English (US)",

volume = "66",

pages = "6565--6568",

journal = "Tetrahedron",

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TY - JOUR

T1 - Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation

AU - Rueping, Magnus

AU - Stoeckel, Mirjam

AU - Sugiono, Erli

AU - Theissmann, Thomas

PY - 2010/8/14

Y1 - 2010/8/14

N2 - 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.

AB - 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.

KW - Asymmetric reduction

KW - Brønsted acid

KW - Flumequine

KW - Levofloxacine

KW - Organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=77955656206&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2010.04.091

DO - 10.1016/j.tet.2010.04.091

M3 - Article

AN - SCOPUS:77955656206

SN - 0040-4020

VL - 66

SP - 6565

EP - 6568

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation

Abstract

Keywords

ASJC Scopus subject areas

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