Twisted Amides as Selective Acylating Agents for Hydroxyl Groups under Neutral Conditions:  Models for Activated Peptides during Enzymatic Acyl Transfer Reaction

The highly twisted amide 2 served as a selective acylating agent for diols under neutral conditions. The reaction of primary−secondary diols with 2 led to the corresponding primary alkyl monopivalates. For diols containing alcoholic and phenolic hydroxyl groups, alcoholic hydroxyl groups were select...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 1996-08, Vol.61 (17), p.5932-5938
Hauptverfasser: Yamada, Shinji, Sugaki, Takayuki, Matsuzaki, Kazuhiro
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The highly twisted amide 2 served as a selective acylating agent for diols under neutral conditions. The reaction of primary−secondary diols with 2 led to the corresponding primary alkyl monopivalates. For diols containing alcoholic and phenolic hydroxyl groups, alcoholic hydroxyl groups were selectively acylated under neutral conditions, whereas, the opposite selectivity was observed under basic conditions, similar to the cases using acyl halides or acid anhydrides. Although 1 and 3 were unreactive to alcohols, 5−10 having substituent groups at C-4 were reactive to alcohols to give the corresponding acetates or benzoates.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9522015