Aminomethylhydroxylation of alkenes: Exploitation in the synthesis of scaffolds for small molecule libraries

被引：11

作者：

Colomer, Ignacio ^{[1
]}

Adeniji, Ololade ^{[1
]}

Burslem, George M. ^{[1
,2
]}

Craven, Philip ^{[1
,2
]}

Rasmussen, Martin Ohsten ^{[3
]}

Willaume, Anthony ^{[3
]}

Kalliokoski, Tuomo ^{[4
]}

Foster, Richard ^{[1
,2
]}

Marsden, Stephen P. ^{[1
]}

Nelson, Adam ^{[1
,2
]}

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

[2] Univ Leeds, Astbury Ctr Struct Mol Biol, Leeds LS2 9JT, W Yorkshire, England

[3] Edelris, F-69003 Lyon, France

[4] Lead Discovery Ctr, D-44227 Dortmund, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2015年 / 23卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

Small molecule libraries; Cycloaddition; 1,3-Amino alcohols; IONIZATION-REARRANGEMENT REACTIONS; EPOXIDATION; GENERATION; AMIDES; IONS;

D O I：

10.1016/j.bmc.2015.01.058

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The application of [4+2] cycloadditions between alkenes and an N-benzoyl iminium species, generated in situ under acidic conditions, is described in the synthesis of diverse molecular scaffolds. The key reaction led to the formation of cyclic imidates in good yield and with high regioselectivity. It was demonstrated that the cyclic imidates may be readily converted into 1,3-amino alcohols. Incorporation of orthogonally-reactive functionality, such as aryl and alkyl bromides, into the cycloaddition substrates enabled the synthesis of additional scaffolds. For one scaffold, the synthesis of exemplar screening compounds was undertaken to demonstrate potential value in small molecule library production. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2736 / 2740

页数：5

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