Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts

被引：13

作者：

Destro, Dario ^{[1
]}

Sanchez, Sandra ^{[1
]}

Cortigiani, Mauro ^{[1
]}

Adamo, Mauro F. A. ^{[1
]}

机构：

[1] Royal Coll Surgeons Ireland, CSCB, Dept Pharmaceut & Med Chem, 123 St Stephens Green, Dublin 2, Ireland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 24期

基金：

爱尔兰科学基金会;

关键词：

ASYMMETRIC CONJUGATE ADDITION; ENANTIOSELECTIVE CYCLOPROPANATION; MEDIATED AMIDATION; AMIDES; ACID; 4-NITRO-5-STYRYLISOXAZOLES; 1,2,3-TRIAZOLES; ALKYLATION; BOND;

D O I：

10.1039/c7ob00799j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report a two-step sequence for the preparation of amides starting from azides and enolisable aldehydes. The reaction proceeded via the formation of triazoline intermediates that were converted into amides via Lewis acid catalysis. Preliminary studies on the preparation of triazolines under chiral phase transfer catalysis are also presented, demonstrating that enantioenriched amides could be prepared from achiral aldehydes in moderate to low enantioselectivity.

引用

收藏

页码：5227 / 5235

页数：9

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