The Stetter reaction : synthesis of complex spiro Bis-indanes and studies on quaternary centre formation
| dc.contributor.advisor | Gravel, Michel | en_US |
| dc.contributor.committeeMember | Krol, Ed S. | en_US |
| dc.contributor.committeeMember | Majewski, Marek | en_US |
| dc.contributor.committeeMember | Dimmock, Jonathan R. | en_US |
| dc.creator | Holmes, Janice | en_US |
| dc.date.accessioned | 2013-09-16T19:52:19Z | |
| dc.date.available | 2013-09-16T19:52:19Z | |
| dc.date.created | 2012-09 | en_US |
| dc.date.issued | 2013-07-29 | en_US |
| dc.date.submitted | September 2012 | en_US |
| dc.description.abstract | This work covers recent advances in the Stetter reaction, including two novel domino Stetter reactions and preliminary studies on quaternary center formation via the intermolecular Stetter reaction. The N-heterocyclic carbene (NHC) catalyzed domino Stetter-aldol-Michael dimerization of o-formyl chalcone derivatives 36 affords spiro bis-indane homo-dimers 38 in good yields and moderate to high diastereomeric ratios. Three carbon-carbon bonds, including the hindered quaternary center at the spiro ring junction, form at a remarkable rate under mild reaction conditions. Spiro bis-indanes 39 are also produced in moderate to good yields through the Stetter-aldol-aldol reactions of o-formyl chalcones 36 with phthalaldehyde derivatives 27. The scope, limitations, and potential applications of these remarkable complexity-generating domino reactions are discussed. Preliminary results in the formation of quaternary centers via the intermolecular Stetter reaction are also disclosed. The viability of β,β-disubstitued Meldrum’s acid, diethyl malonate, and malononitrile alkylidenes as well as diphenylcyclopropenone and 3-phenylcyclobutenone as acceptors in the Stetter reaction are discussed. | en_US |
| dc.identifier.uri | http://hdl.handle.net/10388/ETD-2012-09-523 | en_US |
| dc.language.iso | eng | en_US |
| dc.subject | Stetter reaction | en_US |
| dc.subject | carbenes | en_US |
| dc.subject | organocatalysis | en_US |
| dc.subject | umpolung | en_US |
| dc.subject | domino reactions | en_US |
| dc.title | The Stetter reaction : synthesis of complex spiro Bis-indanes and studies on quaternary centre formation | en_US |
| dc.type.genre | Thesis | en_US |
| dc.type.material | text | en_US |
| thesis.degree.department | Chemistry | en_US |
| thesis.degree.discipline | Chemistry | en_US |
| thesis.degree.grantor | University of Saskatchewan | en_US |
| thesis.degree.level | Masters | en_US |
| thesis.degree.name | Master of Science (M.Sc.) | en_US |