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

Ignacio Colomer, Ololade Adeniji, George M. Burslem, Philip Craven, Martin Ohsten Rasmussen, Anthony Willaume, Tuomo Kalliokoski, Richard Foster, Stephen P. Marsden, Adam Nelson

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)2736-2740
Number of pages5
JournalBioorganic & Medicinal Chemistry
Issue number11
Early online date10 Feb 2015
Publication statusPublished - 1 Jun 2015


  • Small molecule libraries
  • Cycloaddition
  • 1,3-Amino alcohols


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