Multicomponent Synthesis of a N-Protected α-Amino Ester: Ethyl 2-((4-Methoxyphenyl)amino)-3-phenylpropanoate

被引：8
|
作者：
Le Gall, Erwan [1 ,2 ]
Pignon, Antoine [1 ]
机构：
[1] Univ Paris Est Creteil Val de Marne, Inst Chim & Mat Paris Est, UMR CNRS 7182, F-94320 Thiais, France
[2] Univ Paris Est Creteil Val de Marne, Inst Univ Technol Creteil Vitry, F-94400 Vitry Sur Seine, France
来源：
JOURNAL OF CHEMICAL EDUCATION | 2012年 / 89卷 / 09期
关键词：
Second-Year Undergraduate; Laboratory Instruction; Organic Chemistry; Hands-On Learning/Manipulatives; Amino Acids; Esters; Gas Chromatography; Natural Products; Organometallics; Synthesis; MANNICH-TYPE REACTIONS; ACID-DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; 3-COMPONENT REACTION; STEREOSELECTIVE SYNTHESIS; ORGANOBORONIC ACIDS; BORONIC ACIDS; CHIRAL AMINES; ALDEHYDES; ALCOHOLS;
D O I：
10.1021/ed200819f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
This laboratory experiment describes the preparation of a N-protected phenylalanine ethyl ester by a zinc-mediated Mannich-like multicomponent reaction between benzyl bromide, p-anisidine, and ethyl glyoxylate. The one-step reaction involves the in situ metallation of benzyl bromide into a benzylzinc reagent and its addition onto imine (Barbier conditions). The multicomponent procedure is suitable for a 4-to-5 h undergraduate organic laboratory.
引用
收藏
页码：1190 / 1193
页数：4
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