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Five-membered secondary amine heterocycles containing an alpha-heteroatom were prepared and shown to be ineffective as catalysts for the iminium ion catalysed Diels-Alder reaction between cinnamaldehyde and cyclopentadiene. Their six-membered counterparts proved to be highly active catalysts. In stark contrast, the catalytic activity observed when comparing the non alpha-heteroatom cyclic amines proline methyl ester and methyl pipecolinate showed the five-membered ring amine was significantly more active. Concurrent density functional theoretical calculations suggest a rationale for the observed trends in reactivity, highlighting that LUMO activation through an iminium ion intermediate plays a key role in catalytic activity.
Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Synthetic Route of 39657-45-9, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 39657-45-9, in my other articles.
Reference：
Oxazolidine – Wikipedia,
Oxazolidine | C3H1279NO – PubChem