Bio-Based Amides from Renewable Isosorbide by a Direct and Atom-Economic Boric Acid Amidation Methodology

被引：18

作者：

Janvier, Marine ^{[1
]}

Moebs-Sanchez, Sylvie ^{[1
]}

Popowycz, Florence ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, INSA,UMR 5246, CPE Lyon,ICBMS,Equipe Chim Organ & Bioorgan, 20 Ave Albert Einstein, F-69621 Villeurbanne, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 13期

关键词：

Organocatalysis; Carbohydrates; Amino acids; Amides; NONACTIVATED CARBOXYLIC-ACIDS; DIELS-ALDER REACTION; IONIC LIQUIDS; CHIRAL AUXILIARIES; BOND FORMATION; POTENTIAL INHIBITORS; CATALYZED AMIDATION; EFFICIENT SYNTHESIS; ROOM-TEMPERATURE; SERINE-PROTEASE;

D O I：

10.1002/ejoc.201600186

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The functionalization of bio-sourced isohexides has proved challenging over the last number of years, especially in polymer and medicinal chemistry. We report herein the synthesis of bio-based amido-isohexides by the known boric acid catalysed amidation reaction. The coupling reaction was successfully performed with aliphatic and aromatic carboxylic acids. The extension of the scope of the reaction to eight Boc-protected amino acids is also described, the products being obtained in moderate to good yields. A preliminary screening of these new potential organocatalysts was carried out for the aldolization of isatin.

引用

页码：2308 / 2318

页数：11

共 72 条

[51] Asymmetric Horner-Wadsworth-Emmons reaction utilizing isomannide and isosorbide derivatives as chiral auxiliaries [J].