Synthesis of vinca alkaloids and related compounds XCII. Umpolung reactions of enamines through enammonium salts

Authors
Lukacs, A Szabo, L Baitz-Gacs, E Bombicz, P Dobo, A Kalaus, G Szantay, C
Citation
A. Lukacs et al., Synthesis of vinca alkaloids and related compounds XCII. Umpolung reactions of enamines through enammonium salts, HETEROCYCLE, 48(12), 1998, pp. 2507-2520
Citations number
6
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
48
Issue
12
Year of publication
1998
Pages
2507 - 2520
Database
ISI
SICI code
0385-5414(199812)48:12<2507:SOVAAR>2.0.ZU;2-A
Abstract
Preparation of enammonium salt from enamine causes Umpolung, i.e. reverses the reactivity of the original compound. Consequently salt (1) or (9) can b e reacted with cyanide anion which attacks C-1 resulting either in unsatura ted cyanide (11) or rearranged products like 5, 12, 13.