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.
Original language | English |
---|---|
Pages (from-to) | 4002-4007 |
Number of pages | 6 |
Journal | Tetrahedron |
Volume | 70 |
Issue number | 26 |
DOIs | |
Publication status | Published - 1 Jul 2014 |
Keywords
- Asymmetric scaffold
- ATAC scaffold
- Orthogonal protecting groups
- TAC scaffold
- Tripodal scaffold