4.4 Article

The α-effect in cyclic secondary amines: new scaffolds for iminium ion accelerated transformations

Journal

TETRAHEDRON
Volume 65, Issue 48, Pages 9961-9966

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.10.009

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Funding

  1. EPSRC Mass Spectrometry Service
  2. Engineering and Physical Sciences Research Council [GR/S69337/01, EP/E018718/1] Funding Source: researchfish
  3. EPSRC [EP/E018718/1] Funding Source: UKRI

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Five-membered secondary amine heterocycles containing all 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 all iminium ion intermediate plays a key role ill catalytic activity. (C) 2009 Elsevier Ltd. All rights reserved.

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