Tetrahedron

Studies on the synthesis of 8-alkyl-8-aryl-2-azabicyclo [3.3. 1] nonan-7-ones. A short synthetic route to functionalized 8-alkyl derivatives

J Bonjoch, N Casamitjana, J Quirante, C Garriga…

Index: Bonjoch, Josep; Casamitjana, Nuria; Quirante, Josefina; Garriga, Carmer; Bosch, Joan Tetrahedron, 1992 , vol. 48, # 15 p. 3131 - 3138

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Citation Number: 6

Abstract

Two approaches to 8-alkyl-8-aryl-2-azabicyclo [3.3. 1] nonan-7-ones are explored. They are based on the cyclization of an α-alkyl α-aryl ketone upon an iminium salt generated from 2- cyanopiperidine 13 and on the arylation of 8-alkyl-2-azabicyclo [3.3. 1] nonan-7-one 20. An efficient, short synthetic route to 8-alkyl-2-azabicyclo [3.3. 1] nonan-7-ones, using phosphonate 16 as a 5-functionalized 2-oxopentyl synthon, is reported.