Thesis advisor: James P. Morken / This dissertation details the development of several enantioselective or stereospecific transformations involving organoboronic esters. Chapter one will introduce electrophile-induced boronate rearrangements which underpins much of the reactivity that will be discussed in subsequent chapters. In chapter two the conjunctive cross-coupling reaction is presented. Its development and application to the synthesis of non-racemic boronic esters, along with its application to the synthesis of enantioenriched allylic boronic esters, will be discussed. In chapter three the cross-coupling of geminal bis(boronic) esters is introduced and the development of a method to employ them in cross-coupling with alkenyl bromides, affording enantioenriched substituted allylic boronic esters is outlined. In chapter four we highlight the utility of allylic boronic esters, and detail the development of a cross-coupling reaction that involves the use of these substrates and halide electrophiles to furnish enantiomerically enriched products containing all carbon quaternary stereocenters. Finally, in chapter five we describe the development of a metalfree amination reaction of organoboron compounds, which is able to deliver otherwise difficult-to-access enantiomerically enriched α-tertiary amines. / Thesis (PhD) — Boston College, 2018. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.
| Identifer | oai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_108038 |
| Date | January 2018 |
| Creators | Edelstein, Emma Kate |
| 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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