Journal of Organic Chemistry p. 1019 - 1026 (1985)
Update date:2022-08-03
Topics:
Meyers, A. I.
Edwards, Philip D.
Bailey, Thomas R.
Jagdmann, G. Erik
Saturated heterocycles, as their tert-butylformamidines, may be transformed into enamidines, by metalation-selenation-elimination.These enamidines are valuable precursors to 2-substituted, 2,4-disubstituted, and 2,4,6-trisubstituted pyrrolidines, piperidines, and perhydroazepines, prepared in a regiospecific manner.The method is demonstrated by the synthsesis of selenopsin A and the red fire ant venom.The use of acyclic enamidines is displayed as a homologation reagent which converts carbonyl compounds to higher alkyl derivatives.
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