Thesis advisor: James P. Morken / This dissertation aims to design and develop novel and synthetically useful catalytic enantioselective C-C bond-forming reactions that employ a newly uncovered 3,3'-reductive elimination of bis(allyl)metal species. This elementary transformation allows for new routes for the enantioselective construction of a range of important motifs found in natural products. Enantiomerically enriched Z-allylic alcohols are readily accessed through the Ni-catalyzed allylation of trans,trans-dienals. Importantly, the first example of branch- and enantioselective allyl-allyl cross-coupling is presented as well, suitable for the construction of compounds bearing tertiary and quaternary carbon centers. With the aim to broaden the application of above described transformations, this dissertation also presents the development of highly efficient and convenient methods for the syntheses of substituted and functionalized allylic boronates. / Thesis (PhD) — Boston College, 2012. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.
| Identifer | oai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_101159 |
| Date | January 2012 |
| Creators | Zhang, Ping |
| Publisher | Boston College |
| Source Sets | Boston College |
| Language | English |
| Detected Language | English |
| Type | Text, thesis |
| Format | electronic, application/pdf |
| Rights | Copyright is held by the author, with all rights reserved, unless otherwise noted. |
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