Stereoselective Synthesis of Multisubstituted α-fluoro-β-lactams

被引：3

作者：

Tarui, Atsushi ^{[1
]}

Karuo, Yukiko ^{[1
]}

Sato, Kazuyuki ^{[1
]}

Kawai, Kentaro ^{[1
]}

Omote, Masaaki ^{[1
]}

机构：

[1] Setsunan Univ, Fac Pharmaceut Sci, Hirakata, Osaka 5730101, Japan

来源：

CURRENT ORGANIC CHEMISTRY | 2020年 / 24卷 / 18期

基金：

日本学术振兴会;

关键词：

Fluorine; beta-lactam; beta-amino acid; stereoselective synthesis; cross-coupling; Reformatsky reaction; ENANTIOSELECTIVE REFORMATSKY REACTION; NEGISHI CROSS-COUPLINGS; CATALYTIC ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ETHYL BROMODIFLUOROACETATE; BROMO AMIDES; ONE-POT; SECONDARY; ARYLATION; ALDEHYDES;

D O I：

10.2174/1385272824666200221114707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Lactams, found in beta-lactam antibiotics, are the structurally distorted cyclic compounds being subjected to nucleophilic acyl substitution reaction. alpha-Fluorination of beta-lactams is a simple and expedient approach to control the reactivity of beta-lactam ring toward nucleophilic attack, which would hopefully lead to the new design of future antibiotics. From the viewpoint of obtaining multisubstituted alpha-fluoro-beta-lactams, alpha-bromo-afluom-beta-lactams are considered as key compounds for structure functionalization, including nucleophilic substitution reaction, aldol-type reaction and metal-catalyzed cross-coupling reaction. All the reactions can be conducted smoothly to afford a variety of multisubstituted alpha-fluoro-beta-lactams. During the course of the examination, chiral alpha,alpha-difluoro-beta-lactams and alpha-bromo-beta-fluoro-alpha-lactams are successfully obtained, which are considered potent precursors for making stereocontrolled multisubstituted alpha-fluoro-beta-lactams.

引用

页码：2169 / 2180

页数：12

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