The asymmetric synthesis of arylglycines
| dc.contributor.author | Hendrix, James A., author | |
| dc.contributor.author | Williams, Robert M., advisor | |
| dc.date.accessioned | 2022-11-28T17:44:53Z | |
| dc.date.available | 2022-11-28T17:44:53Z | |
| dc.date.issued | 1992 | |
| dc.description.abstract | The asymmetric synthesis of several arylglycines is discussed. Several methods for the coupling of an aromatic group to the chiral bromoglycinates (171, 172) were developed. It was found that the cuprate and Friedel-Crafts couplings provided the desired aryl-coupled glycinates in the greatest yield with excellent selectivity. An oxidative protocol was employed to unmask the oxazinone chiral auxiliary which provided the desired free α-amino acids. A reductive deprotection method was also employed in two unique cases which efficiently gave the arylglycine products. The % ee's ranged from 82 to 94 %. This methodology was further utilized in an approach to the asymmetric synthesis of the bis-arylglycine, actinoidic acid. This study explored the scope of the Stille biphenyl cross-coupling reaction and produced methodology for the synthesis of biphenyl amino acid precursors. | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier.uri | https://hdl.handle.net/10217/235842 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation | Catalog record number (MMS ID): 991018963979703361 | |
| dc.relation | QD431.H46 1992 | |
| dc.relation.ispartof | 1980-1999 | |
| dc.rights | Copyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright. | |
| dc.subject.lcsh | Amino acids -- Synthesis | |
| dc.subject.lcsh | Asymmetric synthesis | |
| dc.subject.lcsh | Glycine | |
| dc.title | The asymmetric synthesis of arylglycines | |
| dc.type | Text | |
| dcterms.rights.dpla | This Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). | |
| thesis.degree.discipline | Chemistry | |
| thesis.degree.grantor | Colorado State University | |
| thesis.degree.level | Doctoral | |
| thesis.degree.name | Doctor of Philosophy (Ph.D.) |
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