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Regiospecific O-alkylation of δ-tetronic acids under mitsunobu-reaction conditions

✍ Scribed by Joginder S Bajwa; Robert C Anderson

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
195 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

An improved procedure for regiospecific 0-alkylation of b-tetronic acids with primary and secondary alcohols, based upon Mitsunobu conditions, is presented. The reaction conditions are very mild and compatible with a variety of hydroxyl protecting groups such as MOM, t-BuMezSi, isopropylidine and esters.

📜 SIMILAR VOLUMES

An unexpected migration of O-silyl group
An unexpected migration of O-silyl group under Mitsunobu reaction conditions
✍ Ramu Sridhar Perali; Suresh Mandava; Venkata Rao Chunduri 📂 Article 📅 2011 🏛 Elsevier Science 🌐 French ⚖ 1018 KB

A 1,4 O?O silyl migration followed by nucleophilic substitution with phthalimide was observed under Mitsunobu reaction conditions. This one step secondary alcohol protection and primary alcohol substitution with N-nucleophiles was extended to a variety of 2-hydroxyethyl trialkylsilylether derivative