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

页码：1190 / 1193

页数：4

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