N-alkenyl aziridines are a unique class of molecules that do not behave as typical enamines as a result of the inability of the nitrogen atom lone-pair of electrons to delocalize. The attenuated nucleophilicity of these enamines presents opportunities for selective functionalization and reactivity not available to classical enamines. An operationally simple and mild copper-mediated
coupling has been developed that facilitates the preparation of a broad range of N-alkenyl
aziridines not available through existing methods. The preparation and reactivity of highly functionalized N-alkenyl aziridines are reported. Also reported is the application of the chemoselective amine/aldehyde/alkyne (A3) multicomponent coupling involving amphoteric aziridine aldehydes as the aldehyde component. This coupling allows access to propargyl amines
with pendent aziridine functionality.
Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:OTU.1807/24235 |
Date | 05 April 2010 |
Creators | Afagh, Nicholas A. |
Contributors | Yudin, Andrei |
Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
Language | en_ca |
Detected Language | English |
Type | Thesis |
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