Readily accessible chiral at nitrogen cage structures

Julian Rowley, Sze Chak Yau, Benson M Kariuki, Alan Kennedy, Nick Tomkinson

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The reaction of glycine-N-methyl amide with paraformaldehyde in the presence of ytterbium triflate (1 mol%) leads to a novel cage structure 6 which is chiral at nitrogen. Single crystal X-ray analysis and DFT calculations suggest this cage structure is rigid and adopts a single low energy conformation. Use of
single enantiomer α-amino amides results in two diastereomeric tertiary amines that differ in their absolute configuration at nitrogen. These diastereoisomers interconvert under acidic conditions but are configurationally stable under basic conditions and can be readily separated by either crystallisation or column
chromatography. By reacting racemic chiral α-amino amides a third diastereomeric cage can also be isolated through this reaction protocol. Preparation of mixed cages by reacting two different α-amino amides is also possible allowing for greater structural diversity in the products to be attained. Preliminary mechanistic studies show that all three methylene units in the cage structure are labile and can be replaced under acidic reaction conditions.
Original languageEnglish
Pages (from-to)2198-2205
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number13
DOIs
Publication statusPublished - 6 Mar 2013

Keywords

  • nitrogen cage structures
  • paraformaldehyde
  • biomolecular chemistry

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