Multistep Flow Procedure for the Waste-Minimized Preparation of N-Boc-β-Amino Ketones

被引：10

作者：

Angelini, Tommaso ^{[1
]}

Bonollo, Simona ^{[1
]}

Ballerini, Eleonora ^{[1
]}

Lanari, Daniela ^{[2
]}

Maggi, Raimondo ^{[3
]}

Piermatti, Oriana ^{[1
]}

Sartori, Giovanni ^{[3
]}

Vaccaro, Luigi ^{[1
]}

机构：

[1] Univ Perugia, CEMIN Dipartimento Chim, Lab Green Synthet Organ Chem, I-06123 Perugia, Italy

[2] Univ Perugia, Dipartimento Chim & Tecnol Farmaco, I-06123 Perugia, Italy

[3] Univ Parma, Dipartimento Chim, Clean Synthet Methodol Grp, I-43124 Parma, Italy

来源：

JOURNAL OF FLOW CHEMISTRY | 2014年 / 4卷 / 01期

关键词：

azides; green chemistry; enones; solvent-free conditions; polystyrene-supported catalysts; AZA-MICHAEL REACTION; ALPHA; BETA-UNSATURATED KETONES; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITIONS; 1,3-AMINO ALCOHOLS; GREEN CHEMISTRY; POLYSTYRYL-BEMP; EPOXIDES;

D O I：

10.1556/JFC-D-13-00027

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A clean and efficient protocol for the synthesis of a wide variety of N-Boc-beta-amino ketones 3a-g has been defined using flow approach. The multistep procedure is based on the beta-azidation of unsaturated ketones, consecutive reduction of the azido group, and concomitant amino group protection, and furnishes the desired products in good yields and very low E-factors ranging from 3.1 to 5.6. In batch conditions and by water as reaction medium, poorer yields and complicated reaction mixtures are obtained. Adoption of the flow approach, which combines transformations performed in solvent-free conditions and in EtOAc, has been essential in order to avoid side reactions, poisoning of the reduction catalyst, and use of minimal amount of reactants.

引用

页码：40 / 43

页数：4

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