Journal of the American Chemical Society

Aza Diels-Alder reactions in aqueous solution: cyclocondensation of dienes with simple iminium salts generated under Mannich conditions

SD Larsen, PA Grieco

Index: Larsen, Scott D.; Grieco, Paul A. Journal of the American Chemical Society, 1985 , vol. 107, # 6 p. 1768 - 1769

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Citation Number: 241

Abstract

Diels-Alder strategy offers a mild and highly practical alternative to the pyrolytic conditions cited above. Moreover, the methodology should prove generally applicable to the synthesis of a number of alkaloids embodying a bridgehead nitrogen. In order to expand the scope of this reaction we examined the cyclocondensation of dienyl aldehyde gSc with benzylamine hydrochloride. Slow addition of 9 over 20 h to a 1. OM solution of benzylamine ...

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