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Paper | Regular issue | Vol 48, No. 12, 1998, pp.2507-2520
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8266
Synthesis of Vinca Alkaloids and Related Compounds XCII. Umpolung Reactions of Enamines through Enammonium Salts

András Lukács, Lajos Szabó, Eszter Baitz-Gács, Petra Bombicz, András Dobó, György Kalaus, and Csaba Szántay*

*Institute of Inorganic Chemistry, Technical University of Budapest, Gellért tér 4, H-1521 Budapest, Hungary

Abstract

Preparation of enammonium salt from enamine causes Umpolung, i.e. reverses the reactivity of the original compound. Consequently salt (1) or (9) can be reacted with cyanide anion which attacks C1 resulting either in unsaturated cyanide (11) or rearranged products like 5, 12, 13.