Date of Award
Dr. LuAnne McNulty
Dr. John Esteb
The 2, 6-disubstitued dihydropyran is produced by a two step process, involving a Suzuki Miyaura Cross Coupling reaction followed by anintramolecular ring closing Michael Addition reaction. In this project a vinyl boronic acid, 6-(2-phenylethenyl)-2-hydroxy-I,2-oxaborole, was coupled with cis-ethyl-iodo-acrylate to yield ethyI 2E, 4Z, 8E-9-phenyl-7-hydroxy-2, 4, 8-nonatrienoate, which is capable of undergoing an intramolecular Michael addition to form the dihydropyran. The geometry of the cis enolate and the conjugated double bonds of the coupled product are such that under basic conditions a Michael addition is feasible. Throughout the project, the reaction conditions for high yields of Suzuki product were determined. Dihydropyrans were produced and verified by proton NMR. It was also established that dihydropyrans can be prepared in a single-pot synthesis, although this method is not yet optimized.
Wright, James Zachary, "Formation of Dihydropyran by a Two Step Process" (2010). Undergraduate Honors Thesis Collection. Paper 80.