The synthesis and utilization of geometrically defined olefins
Abstract/Contents
- Abstract
- The catalytic, and atom economic synthesis of stereodefined olefins remains a major challenge in organic synthesis. Stereodefined olefins are integral in controlling molecular shape and serve as instrumental functional groups for further stereoselective transformations. The following work was focused on the development of more efficient methods towards stereodefined olefins, and on the development of stereoselective functionalizations of these olefin products. Herein we report the first general utilization of 1,1 disubstituted olefins, as well as 1,2-disubstituted olefins in the Ru-catalyzed alkene--alkyne coupling reaction. The products of these reactions were used towards the asymmetric synthesis of aminocyclopentitols, 1,2-amino alcohols, and extended polyketide motifs. Additionally these pursuits led the simultaneous discovery of a general atom economic method for the isomerization of N-allyl amides to form Z-di-, tri-, and tetrasubstituted enamides with exceptional geometric selectivity. Applications of these geometrically defined enamides toward the synthesis of cis vicinal amino alcohols and tetrasubstituted α-borylamido complexes were investigated. Finally we developed new methods towards the synthesis of a particularly interesting class of stereodefined enamides, vinyl nucleotides. Utilization of these building blocks towards the synthesis of nucleotide derivatives led to the discovery of a novel asymmetric Pd catalyzed iodoetherification reaction.
Description
| Type of resource | text |
|---|---|
| Form | electronic resource; remote; computer; online resource |
| Extent | 1 online resource. |
| Place | California |
| Place | [Stanford, California] |
| Publisher | [Stanford University] |
| Copyright date | ©2018 |
| Publication date | 2018; 2018 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Cregg, James Joseph |
|---|---|
| Degree supervisor | Trost, Barry M |
| Thesis advisor | Trost, Barry M |
| Thesis advisor | Burns, Noah |
| Thesis advisor | Waymouth, Robert M |
| Degree committee member | Burns, Noah |
| Degree committee member | Waymouth, Robert M |
| Associated with | Stanford University, Department of Chemistry. |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | James Joseph Cregg. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2018. |
| Location | electronic resource |
Access conditions
- Copyright
- © 2018 by James Joseph Cregg
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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