有机催化氮杂迈克尔加成反应的动力学和机理：烯胺中间体的直接观察。
Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates.
机构信息
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13 (Haus F), 81377 München, Germany.
出版信息
Chem Commun (Camb). 2012 May 11;48(37):4504-6. doi: 10.1039/c2cc31224g. Epub 2012 Mar 28.
PMID:22453687
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.
摘要
咪唑 1a-g 与亚胺离子 2 的 CC 双键加成，其反应速率常数符合方程 log k = s(N)(N + E)。在加成物 3 中，咪唑鎓单元上的质子不利于向烯胺片段迁移，这也是咪唑不能参与亚胺活化的氮杂-Michael 加成反应的原因。
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