Synthesis of (.+-.)-. omega.-aza [xy 1] bicycloalkanes by an intramolecular Mannich reaction

…, S Toeteberg-Kaulen, H Rapoport

Index: Petersen, John S.; Toeteberg-Kaulen, Sabine; Rapoport, Henry Journal of Organic Chemistry, 1984 , vol. 49, # 16 p. 2948 - 2953

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Citation Number: 33

Abstract

Nine acyclic acetal ketal benzylamines have been synthesized and their cyclization reactions in acidic methanol have been examined. In three cases, bicyclic amines-a tropane, a granatanine, and a homotropane-are formed. In five cases, cyclic iminium salts which do not undergo further bicyclization are formed, and these salts were reduced to afford three 2, 5-disubstituted pyrrolidines and two substituted piperidines. In the one case requiring ...