Date Approved

7-12-2015

Date Posted

6-22-2016

Degree Type

Open Access Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Committee Member

Harriet Lindsay, Ph.D, Chair

Committee Member

Cory Emal, Ph.D.

Committee Member

Ingo Janser, Ph.D.

Abstract

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 SN2 pathway can be increased in some reactions by decreasing the polarity of the solvent.

Included in

Chemistry Commons

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