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.
","abstract_html":"<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>","abstract_has_math":false,"creators":["Desai, Hinalbahen Sanket"],"institution":null,"degree_name":"Master of Science (MS)","degree_level":"Open Access Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Harriet Lindsay, Ph.D, Chair","Cory Emal, Ph.D.","Ingo Janser, Ph.D."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-07-12T07:00:00Z","date_published":"2015-07-12T07:00:00Z","updated_at":"2026-07-24T02:17:06Z","subjects":["amines","epoxy compounds","amino alcohols","Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://commons.emich.edu/theses/639","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Harriet Lindsay, Ph.D, Chair","Cory Emal, Ph.D.","Ingo Janser, Ph.D."]},{"key":"dc:creator","label":"Author","values":["Desai, Hinalbahen Sanket"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2016-06-22T07:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Open Access Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (MS)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["amines","epoxy compounds","amino alcohols","Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://commons.emich.edu/theses/639"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:title","label":"Title","values":["Microwave-assisted synthesis of ß-amino alcohols"]}]}],"canonical_facts":{"dc:contributor":["Harriet Lindsay, Ph.D, Chair","Cory Emal, Ph.D.","Ingo Janser, Ph.D."],"dc:creator":["Desai, Hinalbahen Sanket"],"dc:date.available":["2016-06-22T07:00:00Z"],"dc:description.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.
"],"dc:identifier":["https://commons.emich.edu/theses/639"],"dc:subject":["amines","epoxy compounds","amino alcohols","Chemistry"],"dc:title":["Microwave-assisted synthesis of ß-amino alcohols"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Open Access Thesis"],"thesis:degree_name":["Master of Science (MS)"]},"updated_at":"2026-07-24T02:17:06Z"}