Aza-Baylis−Hillman Reactions of N-Tosylated Aldimines with Activated Allenes and Alkynes in the Presence of Various Lewis Base Promoters

The attempted aza-Baylis−Hillman reactions of N-tosylated aldimines with ethyl 2,3-butadienoate,
ethyl penta-2,3-dienoate, penta-3,4-dien-2-one, methyl propiolate, and but-3-yn-2-one have been
systematically investigated in the presence of various nitrogen or phosphine Lewis base promoters.
We found that a series of nitrogen-containing heterocyclic compounds, as “abnormal” aza-Baylis−Hillman reaction products, can be formed in the presence of an appropriate Lewis base promoter.
The Lewis base and solvent effects in these reactions have been discussed along with the
corresponding plausible mechanism.

对N-甲酰基亚胺与乙基2,3-丁二烯酸、乙基戊-2,3-二烯酸、戊-3,4-二烯-2-酮、甲基丙烯酸甲酯和丁-3-炔-2-酮所进行的尝试性aza-Baylis−Hillman反应，在多种氮或磷叶立德催化的作用下，进行了系统的探究。研究发现，在适宜的磷叶立德促进剂存在下，一系列含氮杂环化合物作为‘异常’的aza-Baylis−Hillman反应产物得以形成。同时，对这些反应中的磷叶立德和溶剂效应进行了讨论，并提出了相应的合理机理。