Thesis advisor: James P. Morken / The Suzuki-Miyaura cross-coupling reaction is a common strategy for the formation of a new carbon-carbon bond in organic synthesis. However, intramolecular coupling of allylboron ester and aryl electrophiles has never been reported. Herein, Pd-catalyzed intramolecular cross-coupling of allylboronic pinacol ester and vinyl or aryl bromides is presented. Pt-catalyzed 1,2-diboration of 1,3-dienes give α-chiral bis-allylboronic esters, which can undergo diastereoselective additions to carbonyl electrophiles tethered to vinyl or aryl halides to generate a new allylboronic ester moiety. Under Suzuki coupling conditions, the allylboronic esters moiety and the vinyl bromides in the allylation products can cross-couple in an intramolecular fashion to afford highly substituted four-, five-, and six-membered rings with excellent yields and moderate diastereoselectivity. / Thesis (MS) — Boston College, 2014. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.
| Identifer | oai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_104067 |
| Date | January 2014 |
| Creators | Chang, Weng Kun |
| 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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