Chemical communications

Samarium diiodide-induced intramolecular pinacol coupling of dinitrones: synthesis of cyclic cis-vicinal diamines

JP Ebran, RG Hazell, T Skrydstrup

Index: Ebran, Jean-Philippe; Hazell, Rita G.; Skrydstrup, Troels Chemical Communications, 2005 , # 43 p. 5402 - 5404

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Citation Number: 11

Abstract

Taking into consideration the previous work on SmI 2 -promoted intramolecular cyclisations of ketyl-hydrazones 13 or ketyl-oximes 14 for the formation of five-, six- and seven-membered cyclic amino alcohols, initial efforts were focused on the ability of a nitrone group to undergo intramolecular coupling with either a hydrazone or oxime. Hence, the nitrone hydrazone 1 was first submitted to conditions reported by Sturino and Fallis 13a for promoting ring formation (SmI 2 2.4 ...