Abstract
Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented.
| Original language | English |
|---|---|
| Pages (from-to) | 4399-4412 |
| Number of pages | 14 |
| Journal | Tetrahedron |
| Volume | 60 |
| Issue number | 20 |
| Early online date | 26 Feb 2004 |
| DOIs | |
| Publication status | Published - 10 May 2004 |
Research Groups and Themes
- Organic & Biological
Keywords
- Atropisomeric amides
- Ephedrine
- Imidazolines
- Oxazolidines
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