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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.


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The Enantioselective Synthesis of β-Amin
✍ Charles W. Jefford; James McNulty; Zhi-Hui Lu; Jian Bo Wang 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 German ⚖ 1016 KB

## 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