Chemistry of four-membered cyclic nitrones. 3. Reaction with nucleophilic reagents and stereospecific conversion into 1-hydroxyazetidines

…, S Harkema, GJ Van Hummel

文献索引：Pennings, Marcel L.M.; Reinhoudt, David N.; Harkema, Sybolt; Hummel, Gerrit J. van Journal of Organic Chemistry, 1982 , vol. 47, # 23 p. 4419 - 4425

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被引用次数: 12

摘要

Four-membered cyclic nitrones (1) react with a variety of nucleophiles (MeMgI, CN-, OH-, MeO-, and H-) by stereospecific addition to the C= N bond. Reaction of la with potassium cyanide and with methylmagnesium iodide yields the 1-hydroxyazetidines 2a and 2b, respectively. Reduction of lb with lithium aluminum hydride and with sodium borohydride affords the 1-hydroxyazetidine derivatives 3 and 4, respectively. Sodium hydroxide in ...