Expedient synthesis of a novel asymmetric selectively deprotectable derivative of the ATAC scaffold

Brouwer, A. J., Van De Langemheen, H. and Liskamp, R. M.J. (2014) Expedient synthesis of a novel asymmetric selectively deprotectable derivative of the ATAC scaffold. Tetrahedron, 70(26), pp. 4002-4007. (doi: 10.1016/j.tet.2014.04.084)

Abstract

An efficient multigram scale synthesis of a new asymmetric triazacyclophane scaffold, the ATAC (Asymmetric-TAC) scaffold, bearing three selectively removable groups is described. This scaffold is slightly more rigid than our frequently used TAC (TriAzaCyclophane) scaffold. The synthesis of the required triamine is very high yielding without difficult steps or purifications and was also applied to a much improved synthesis of our original TAC scaffold. Especially the tedious first reaction step, that is, mono-oNBS-protection of a triamine could be omitted. The rigidity of the triazacyclophane ring in both TAC- and ATAC scaffolds has also been investigated using variable temperature 1H NMR experiments.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Liskamp, Professor Robert and Van De Langemheen, Mr Helmus
• Authors: Brouwer, A. J., Van De Langemheen, H., and Liskamp, R. M.J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron
• Publisher: Elsevier Ltd.
• ISSN: 0040-4020
• ISSN (Online): 1873-3581