. alpha.-Amino carbanions via formamidines. Alkylation of pyrrolidines, piperidines, and related heterocycles

AI Meyers, PD Edwards, WF Rieker…

Index: Meyers,A.I.; Edwards,P.D.; Rieker,W.F. Journal of the American Chemical Society, 1984 , vol. 106, p. 3270

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Citation Number: 106

Abstract

Abstract: a-Metalation of piperidine, pyrrolidine, hexahydroazepine, 1, 3-thiazolidine, and 1, 3-thiazane has been accomplished via their N-tert-butylformamidine derivatives. Alkylation of these a-amino carbanions via their lithio or cuprate derivatives leads to good yields of a- substituted heterocycles. Similarly, 1, 2, 5, 6-tetrahydropyridine metalates at the 2 position, but alkylates at the 4 position. Reduction leads to 4-substituted piperidines. Evidence is ...