Inverse electron demand Diels-Alder chemistry of electron deficient chromosome-fused dienes

Nwagbara, Amaizu Joseph (2015) Inverse electron demand Diels-Alder chemistry of electron deficient chromosome-fused dienes. Masters thesis, Memorial University of Newfoundland.

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Abstract

An introduction to inverse electron demand Diels-Alder reaction (IEDDA) chemistry is presented in Chapter one. In Chapter two, work aimed at improving an IEDDA-driven domino reaction leading to 2-hydroxybenzophenone is presented. Chromone-fused electron deficient dienes were synthesized as substrates for IEDDA-driven domino reactions. The reaction between one of these dienes and in situ-generated enamines of cyclobutanone was optimized. The optimized conditions were then applied to a variety of enamines derived from piperidine and various ketones (cyclic and acyclic). In almost all cases, the yields were superior to those obtained using preformed enamines and previously reported conditions for the in situ formation of the enamine. In Chapter three the attempted synthesis of a new chiral [n](1,6)pyrenophane is described. The described synthetic approach mirrors that of a cyclophane previously reported by the Bodwell group, but makes use of cyclohexanone instead of cyclopentanone in the initial IEDDA-based multicomponent reaction. The synthesis was brought to the final step, but none of the target pyrenophane was obtained from the key McMurry/VID reaction.

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