Aminomethylhydroxylation of alkenes: Exploitation in the synthesis of scaffolds for small molecule libraries. Issue 11 (1st June 2015)

• Record Type: Journal Article
• Authors: Colomer, Ignacio; Adeniji, Ololade; Burslem, George M.; Craven, Philip; Rasmussen, Martin Ohsten; Willaume, Anthony; Kalliokoski, Tuomo; Foster, Richard; Marsden, Stephen P.; Nelson, Adam
• Is Part Of: Bioorganic & medicinal chemistry. Volume 23:Issue 11(2015)
• Page Start: 2736
• Page End: 2740
• Publication Date: 2015-06-01
• Subjects: Small molecule libraries -- Cycloaddition -- 1, 3-Amino alcohols; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2015.01.058
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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.