Efficient, two-step synthesis of N-substituted nortropinone derivatives

…, C Boutillon, L Verbraeken, JC Gesquière, A Tartar…

Index: Willand, Nicolas; Folleas, Benoit; Boutillon, Christophe; Verbraeken, Liesbeth; Gesquiere, Jean-Claude; Tartar, Andre; Deprez, Benoit Tetrahedron Letters, 2007 , vol. 48, # 29 p. 5007 - 5011

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Citation Number: 10

Abstract

We describe a novel strategy for the synthesis of N-substituted nortropinone derivatives starting from tropinone. The key step of our synthesis is a reactivity umpolung of tropinone, which yields 8, 8-dimethyl-3-oxo-8-azonia-bicyclo [3.2. 1] octane iodide (IDABO) as a stable and convenient synthetic equivalent of cycloheptadienone.