. alpha.-Amino carbanions. Preparation, metalation, and alkylation of enamidines. Synthesis of piperidine and pyrrolidine natural products and homologation of …

AL Meyers, PD Edwards, TR Bailey…

Index: Meyers, A. I.; Edwards, Philip D.; Bailey, Thomas R.; Jagdmann, G. Erik Journal of Organic Chemistry, 1985 , vol. 50, # 7 p. 1019 - 1026

Full Text: HTML

Citation Number: 62

Abstract

Saturated heterocycles, as their tert-butylformamidines, may be transformed into enamidines, by metalation-selenation-elimination. These enamidines are valuablz precursors to 2-substituted, 2, 4-disubstituted, and 2, 4, 6-trisubstituted pyrrolidines, piperidines, and perhydroazepines, prepared in a regiospecific manner. The methd is demonstrated by the synthesis of solenopsin A and the red fiie ant venom. The use of ...