Abstract
The homochiral phosphinic azides (R,R)-1 and (S,S)-1 were prepared in enantiomerically pure form by resolution of diastereomeric phosphinamides derived from (S)-1-phenylethylamine and (R)-phenylglycine. Irradiation of the azides in methanol induced a photo-Curtius rearrangement to phosphonamidates in which the stereogenic carbon unit migrated to a nitrogen atom. Hydrolysis of the phosphonamidates produced 1-phenylethylamine, which was 99.0% e.e. and of the same configuration as the carbon unit in the starting azide (99.0% retention).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 241-257 |
| Number of pages | 17 |
| Journal | Chirality |
| Volume | 14 |
| Issue number | 2-3 |
| DOIs | |
| State | Published - 2002 |
Keywords
- Carbon-phosphorus bond cleavage
- Curtius reaction
- Phosphinoyl azides
- Stereospecificity
ASJC Scopus subject areas
- Analytical Chemistry
- Catalysis
- Pharmacology
- Drug Discovery
- Spectroscopy
- Organic Chemistry