ORGN 140-8-Aryl menthamine-derived scaffolds for iminium ion catalysis

Ruda, Antonio M. and Cavill, Julie L. and Tomkinson, Nicholas C. O. (2006) ORGN 140-8-Aryl menthamine-derived scaffolds for iminium ion catalysis. Abstracts of papers - American Chemical Society, 232. 140-ORGN. ISSN 0065-7727

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This poster will describe a novel series of mol. scaffolds for the acceleration of iminium ion catalyzed processes. Drawing inspiration from Corey's 8-Ph menthol chiral auxiliary we have developed a concise synthesis of a new family of secondary amines and investigated their catalytic activity in the Diels-Alder reaction. Importantly, starting from (+)-pulegone as the source of chirality the nature of the asym. induction in the catalytic reaction can be altered by use of either the cis- or the trans-catalyst. Our investigations into variation of the nature of the arom. to modulate a proposed face-face π-π interaction in the transition state will also be reported. [on SciFinder(R)]