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Issue 13, 2013
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Readily accessible chiral at nitrogen cage structures

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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.

Graphical abstract: Readily accessible chiral at nitrogen cage structures

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Publication details

The article was received on 19 Dec 2012, accepted on 29 Jan 2013 and first published on 30 Jan 2013

Article type: Paper
DOI: 10.1039/C3OB27458F
Citation: Org. Biomol. Chem., 2013,11, 2198-2205

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    Readily accessible chiral at nitrogen cage structures

    J. H. Rowley, S. C. Yau, B. M. Kariuki, A. R. Kennedy and N. C. O. Tomkinson, Org. Biomol. Chem., 2013, 11, 2198
    DOI: 10.1039/C3OB27458F

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