This dissertation is a combination of both research and teaching experience. Part I will cover research done in the area of organocatalyzed synthesis of optically active 4-substituted 2-cyclohexenones, while Part II will cover teaching experience at University of West Florida. 4-substituted 2-cyclohexenones are important building blocks for natural products. Both racemic and enantioselective syntheses of these small molecules have been reported, however, most methodologies are limited to very few substrates and necessitate four to more number of steps. A two step syntheses of 4-substituted 2-cyclohexenones were recently provided independently by Baran and Nicolaou groups en route to dihydrojunenol and ent-7-epizingiberene respectively. Both groups used base-mediated intramolecular aldol condensation of optically pure monosubstituted acyclic ketoladehydes. Applying Baran's LiOH-mediated aldol condensation to both the benzyl and ethyl substituted ketoaldehydes afforded cyclization products with significant erosion of optical purity. A mechanistic study of the reaction and a reasonable justification of such erosion in optical purity are provided. Inspired by the base-catalyzed aldol condensation, we sought synthesizing optically active 4-substituted 2-cyclohexenones via organocatalyzed Robinson annulation approach (Michael addition-Aldol condensation). Finding a set of organocatalyzed conditions to promote the enolendo intramolecular aldol condensation of acyclic ketoaldehydes with low erosion of optical purity is discussed. Finally a neutral set of organocatalyzed conditions is offered and expanding the methodology to synthesize a library of ten optically active 4-susbtituted 3-cyclohexenones is reported. Part II of this dissertation covers the experience in applying the Seven Principles for Good Practice in teaching organic chemistry II course at University of West Florida. It is generally accepted that organic chemistry is one of the fields where the Seven Principles are least applied. Working as teaching assistant for different organic chemistry professors at FSU was extremely helpful in (1) observing the different teaching strategies applied in classroom and (2) examining the response of students to certain activities done in class, laboratory or recitation. In fall 2010, a chance of applying personal teaching strategies was offered, efforts to apply the seven principles is described, finishing with conclusions. / A Dissertation submitted to the Department of Chemistry and Biochemistry in partial fulfillment of the requirements for the degree of Doctor of
Philosophy. / Fall Semester, 2012. / November 5, 2012. / 4-substituted 2-Cyclohexenones, Aldol condensation, Michael addition, Organocatalyzed, Proline derivative, Seven Principle for Good Practice / Includes bibliographical references. / D. Tyler McQuade, Professor Directing Dissertation; Sherry A. Southerland, University Representative; Qing-Xiang (Amy) Sang, Committee Member; Gregory B. Dudley, Committee Member; Igor V. Alabugin, Committee Member.
| Identifer | oai:union.ndltd.org:fsu.edu/oai:fsu.digital.flvc.org:fsu_183570 |
| Contributors | Houjeiry, Tania Issa (authoraut), McQuade, D. Tyler (professor directing dissertation), Southerland, Sherry A. (university representative), Sang, Qing-Xiang (Amy) (committee member), Dudley, Gregory B. (committee member), Alabugin, Igor V. (committee member), Department of Chemistry and Biochemistry (degree granting department), Florida State University (degree granting institution) |
| Publisher | Florida State University, Florida State University |
| Source Sets | Florida State University |
| Language | English, English |
| Detected Language | English |
| Type | Text, text |
| Format | 1 online resource, computer, application/pdf |
| Rights | This Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). The copyright in theses and dissertations completed at Florida State University is held by the students who author them. |
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