Thesis advisor: Amir H. Hoveyda / We have devised a broadly applicable catalytic cross-metathesis method for stereoretentive synthesis of Z- and E-trisubstituted α,β-unsaturated esters. Several new Mo-bisaryloxide complexes were prepared, and they showed superior efficiency in synthesizing the Z-trisubstituted enoates (vs. corresponding mono-aryloxide pyrrolide complexes). Synthetic utility of the method was demonstrated through several concise syntheses of bioactive triterpenoids and value-added derivatives of prenyl-containing compounds such as citronellal, citronellol, and geraniol, all of which are isolated from essential oils. This transformation offers a valuable alternative to carbonyl olefination approaches such as Wittig and Horner-Wadsworth-Emmons reactions. / Thesis (MS) — Boston College, 2021. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.
Identifer | oai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_109197 |
Date | January 2021 |
Creators | Qin, Can |
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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