Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates |
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| Authors: | Lakhdar Sami Baidya Mahiuddin Mayr Herbert |
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| Affiliation: | Department Chemie, Ludwig-Maximilians-Universit?t München, Butenandtstr. 5-13 (Haus F), 81377 München, Germany. |
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| Abstract: | The imidazoles 1a-g add to the CC-double bond of the iminium ion 2 with rate constants as predicted by the equation log k = s(N)(N + E). Unfavourable proton shifts from the imidazolium unit to the enamine fragment in the adduct 3 account for the failure of imidazoles to take part in iminium-activated aza-Michael additions to enals. |
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