Abstract
dc:description.abstract<p>ß-amino alcohols are common substructures in many biologically active compounds and can also be used as catalysts for asymmetric reactions. One common method for forming these moieties is by ring opening of unsymmetrical epoxides using amines via a substitution reaction. However, the majority of these methods requires excess of reagents, inorganic initiators, and/or extended reaction times. We have developed an efficient, regioselective route to synthesize amino alcohols via microwave-assisted aminolysis of several hindered and unhindered epoxides using amine nucleophiles of varying strengths. Microwave reactions can be done without Lewis acids or promoters, even for the most hindered trisubstituted epoxides. In most of these cases, the reaction requires only a 1:1 ratio of amine to epoxide. Regioselectivity for the S<sub>N</sub>2 pathway can be increased in some reactions by decreasing the polarity of the solvent.</p>
Degree
thesis:*- Name thesis:degree_name
- Master of Science (MS)
- Level thesis:degree_level
- Open Access Thesis
- Discipline thesis:degree_discipline
- Chemistry
- Year dc:date.available
- 2015
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Desai, Hinalbahen Sanket
- Contributors dc:contributor
-
- Harriet Lindsay, Ph.D, Chair
- Cory Emal, Ph.D.
- Ingo Janser, Ph.D.
Subjects
dc:subject × 4Identifiers
dc:identifier.*- Repository record dc:identifier
- https://commons.emich.edu/theses/639
- OAI identifier oai:identifier
- oai:commons.emich.edu:theses-2018