Synthesis of 3-fluoro azetidinone by electrophilic fluorination

被引：21

作者：

Genet, JP ^{[1
]}

Durand, JO ^{[1
]}

Roland, S ^{[1
]}

Savignac, M ^{[1
]}

Jung, F ^{[1
]}

机构：

[1] ZENECA,CTR RECH,F-51064 REIMS,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(96)02217-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easy access to the 3-fluoroazetidinone 4a based on electrophilic fluorination, is reported. The fluorination of the beta-lactam 7 with Differding's N-fluorosulfonimide proceeds stereoselectively, under mild conditions and in good yield. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：69 / 72

页数：4

共 28 条

[1] ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY
BALDWIN, JE
LYNCH, GP
SCHOFIELD, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (10) : 736 - 738
[2] N-FLUORO-N-ALKYLSULFONAMIDES - USEFUL REAGENTS FOR THE FLUORINATION OF CARBANIONS
BARNETTE, WE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) : 452 - 454
[3] A VERSATILE SYNTHESIS OF 1,1-DIOXO 7-SUBSTITUTED CEPHEMS - PREPARATION OF THE HUMAN-LEUKOCYTE ELASTASE (HLE) INHIBITOR 1,1-DIOXO-TRANS-7-METHOXYCEPHALOSPORANIC ACID TERT-BUTYL ESTER
BLACKLOCK, TJ
BUTCHER, JW
SOHAR, P
LAMANEC, TR
GRABOWSKI, EJJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) : 3907 - 3913
[4] HALOGENATED KETENES .7. ON MONOHALOKETENES
BRADY, WT
HOFF, EF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (22) : 6256 - &
[5] NEW FLUORINATING REAGENTS .2. PREPARATION AND SYNTHETIC APPLICATION OF A SACCHARIN DERIVED N-FLUOROSULTAM
DIFFERDING, E
LANG, RW
[J]. HELVETICA CHIMICA ACTA, 1989, 72 (06) : 1248 - 1252
[6] ELECTROCHEMICAL REDUCTION OF NITROGEN-FLUORINE BONDS - RELEVANCE TO THE REACTIVITY OF ELECTROPHILIC FLUORINATING AGENTS
DIFFERDING, E
BERSIER, PM
[J]. TETRAHEDRON, 1992, 48 (09) : 1595 - 1604
[7] NUCLEOPHILIC-SUBSTITUTION VERSUS ELECTRON-TRANSFER .1. ON THE MECHANISM OF ELECTROPHILIC FLUORINATIONS
DIFFERDING, E
RUEGG, GM
[J]. TETRAHEDRON LETTERS, 1991, 32 (31) : 3815 - 3818
[8] DIFFERDING E, 1991, SYNLETT, P187
[9] DURAND JO, 1993, THESIS U PARIS 6
[10] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .4. REGIOSELECTIVE ANODIC MONOFLUORINATION OF 4-THIAZOLIDINONES AND ITS APPLICATION TO THE SYNTHESIS OF MONOFLUORO BETA-LACTAMS
FUCHIGAMI, T
NARIZUKA, S
KONNO, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) : 3755 - 3757

← 1 2 3 →