The asymmetric synthesis of amino acids via glycine enolates
| dc.contributor.author | Im, Myeong-Nyeo, 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 | 1991 | |
| dc.description.abstract | The enolates derived from the optically active D-e rythro-4- (tertbutyloxycarbonyl)-5,6-di phenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (166a) and D- and L-erythro-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6- tetrahydro-4H-1,4-oxazin-2-ones (167a/b) efficiently couple with alkyl halides to afford the corresponding anti-α-monosubstituted oxazinones. The enolate alkylation of the a-monosubstituted oxazinones provides the corresponding α-disubstituted oxazinones. Dissolving-metal reduction of the homologated oxazinones allows the direct preparation of t-BOC protected α-amino acids. In the case of dissolving metal-reducible functionality, hydrogenation over a Pd° catalyst furnishes the zwitterionic amino acids. By employing this protocol the syntheses of complex amino acids such as 2-(tert-butyloxycarbonyl)amino-6-(p-methoxybenzyI)thionohexanoic acid and 2,6-diamino-6-hydroxymethylpimelic acid are discussed. | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier.uri | https://hdl.handle.net/10217/235841 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation | Catalog record number (MMS ID): 991017668619703361 | |
| dc.relation | QD431.I45 1991 | |
| 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 | Glycine | |
| dc.subject.lcsh | Organic compounds -- Synthesis | |
| dc.title | The asymmetric synthesis of amino acids via glycine enolates | |
| 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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