Exploratory studies probing the intermediacy of azomethine ylides in the photochemistry of N-phthaloyl derivatives of α-amino acids and β-amino alcohols
✍ Scribed by Ung Chan Yoon; Chan Woo Lee; Sun Wha Oh; Patrick S Mariano
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 632 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Ab~ract: Exploratory photochemical studies with N-phthaloyl derivatives of glutamic acid, aspartic acid, serine, threonine and analogous carboxylic acids and alcohols have been conducted to determine the generality of azomethine ylide forming decarboxylation and retro-aldol fragmentation reactions. Preferences in the competition between these excited state reaction pathways have been determined by studies with phthalimides which contain both a-amino acid and [3-aminoethanol groups.
📜 SIMILAR VOLUMES
## Abstract L‐Aspartic acid by tosylation, anhydride formation, and reduction with NaBH~4~ was converted into (3__S__)‐3‐(tosylamino)butan‐4‐olide (8; __Scheme 1__). Tretment of 8 with ethanolic trimethylsilyl iodide gave the __N__‐protected deoxy‐iodo‐β‐homoserine ethyl ester 9. The latter, on suc