Open Access Thesis
Master of Science (MS)
β-Amino alcohols are important organic compounds with numerous applications. Commonly β-amino alcohols are prepared by ring opening of epoxides using an amine nucleophile and a catalyst or promoter. Ring opening can take place by the SN1 pathway or the SN2 pathway, but no single catalyst or promoter consistently gives SN2 selectivity. Additionally, long reaction times are often required to obtain adequate yields. We have demonstrated that microwave heating reduces reaction times for the aminolysis of both reactive and unreactive, sterically hindered epoxides. These reactions were accomplished with various amines. In all cases, only one equivalent of amine and epoxide were needed to give good yields and modest to excellent regioselectivity for the SN2 product.
Amino alcohols made by aminolysis and other methods were used to investigate the aza-Cope rearrangement—Mannich cyclization. We proposed that this procedure could be used to produce compounds we could modify and transform into several alkaloids.
D'Souza, Brendan Roberto, "Development of a Microwave-Assisted Epoxide Aminolysis and Investigation of the aza-Cope Rearrangement--Mannich Cyclization for Alkaloid Synthesis" (2007). Master's Theses and Doctoral Dissertations. 16.