Reaction of organolithium reagents with lactim ethers: preparation of cyclic 2-alkyl imines or 2, 2-dialkyl amines

CA Zezza, MB Smith, BA Ross, A Arhin…

Index: Zezza, Charles A.; Smith, Michael B.; Ross, Betsy A.; Arhin, Akwasi; Cronin, Patricia L. E. Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4397 - 4399

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Citation Number: 29

Abstract

The reaction of lactim ethers 1-3 with organolithium reagents has been found to be an effective method for the preparation of cyclic 2-alkyl imines 4-6. The method is most effective for the preparation of 2-aryl and sterically hindered 2-alkyl imines. In addition, treatment of 1- 3 with excess organolithium provides a facile route to the rare cyclic 2, 2-dialkyl amine derivatives 7-9. These reactions are characterized by mild reaction conditions and good ...