Colomer, I, Adeniji, O, Burslem, GM et al. (7 more authors) (2015) Aminomethylhydroxylation of alkenes: Exploitation in the synthesis of scaffolds for small molecule libraries. Bioorganic and Medicinal Chemistry, 23 (11). pp. 2736-2740. ISSN 0968-0896
Abstract
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Keywords: | Small molecule libraries; Cycloaddition; 1,3-Amino alcohols |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 19 Sep 2016 14:08 |
Last Modified: | 19 Sep 2016 14:08 |
Published Version: | http://dx.doi.org/10.1016/j.bmc.2015.01.058 |
Status: | Published |
Publisher: | Elsevier |
Identification Number: | 10.1016/j.bmc.2015.01.058 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:92710 |