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Readily accessible chiral at nitrogen cage structures

Rowley, Julian H., Yau, Sze Chak, Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897, Kennedy, Alan R. and Tomkinson, Nicholas C. O. 2013. Readily accessible chiral at nitrogen cage structures. Organic & Biomolecular Chemistry 11 (13) , pp. 2198-2205. 10.1039/c3ob27458f

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Last Modified: 24 Oct 2022 11:10
URI: https://orca.cardiff.ac.uk/id/eprint/47159

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