The Utilization of Sulfinimines (N-Sulfinyl Imines) in the Asymmetric Synthesis of Substituted Pyrrolidines
| Autor: | Bowen, Kerisha Andrea |
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| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: | |
| Druh dokumentu: | Text |
| DOI: | 10.34944/dspace/823 |
| Popis: | The objective of this research was the development of new methods for the asymmetric synthesis of nitrogen containing compounds. As one part of this goal, 3,4-dihydroxyprolines and their derivatives were prepared from sulfinimines (N-sulfinyl imines). During this project new methods were developed for asymmetric hydroxylation and decarboxylation of 3-oxo-2-carboxylate pyrroldines. The application of this new methodology was realized by the total synthesis of the α- and β-glycosidases inhibitor (+)-lentginosine. It was also found that electrophiles regioselectively add to the 4-position of 3-oxo-2-carboxylate-5-substituted pyrrolidines. The addition is accomplished through lithium diisopropyl amide generation of the pyrrolidine dianion. This addition was also compatible with 3-oxo-2-phosophono-5-substituted pyrroldines. Furthermore air oxidation of these pyrrolidines give the corresponding pyrroles. This procedure represents the first general preparation procedure for 2-phonopyrroles, which have been examined as HIV protease inhibitors. A range of β-amino carbonyl compounds were prepared from N-sulfinyl β-amino Weinreb amides in a concise and efficient procedure. A general method for the preparation of a variety of β-amino carbonyl compounds arose from the addition of an assortment of organometallic reagents to the Weinreb amides. The N-sulfinl β-amino Weinreb amides are prepared by reaction of the potassium enolate of N-methoxy-N-methylacetamide with sulfinimines or lithium N,O-dimethylhydroxylamine with N-sulfinyl β-amino esters. Chemistry Ph.D. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
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