Diastereoselective Synthesis of 2-Amino-4-phosphonobutanoic Acids by Conjugate Addition of Lithiated Schöllkopf's Bislactim Ethers to Vinylphosphonates
| Autor: | Aniana Diaz, Vicente Ojea, M. Carmen Fernandez, María José Ruiz, José M. Quintela |
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| Rok vydání: | 2003 |
| Předmět: |
Models
Molecular Addition reaction Cyclic compound Magnetic Resonance Spectroscopy Vinyl Compounds Lactams Stereochemistry Chemistry Aminobutyrates Organic Chemistry Molecular Conformation Organophosphonates Stereoisomerism Ether Lithium Receptors Metabotropic Glutamate Chemical synthesis chemistry.chemical_compound Molecule Stereoselectivity Enantiomer Ethers Conjugate |
| Zdroj: | The Journal of Organic Chemistry. 68:7634-7645 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | Conjugate additions of lithiated bislactim ethers derived from cyclo-[Gly-Val] and cyclo-[Ala-Val] to alpha-, beta-, or alpha,beta-substituted vinylphosphonates allow direct and stereoselective access to a variety of 3- or 4-monosubstituted and 2,3-, 2,4-, or 3,4-disubstituted 2-amino-4-phosphonobutanoic acids (AP4 derivatives) in enantiomerically pure form. The relative stereochemistry was assigned by X-ray diffraction analysis or NMR study of 1,2-oxaphosphorinane derivatives. Competitive eight-membered "compact" and "relaxed" transition-state structures are invoked to rationalize the stereochemical outcome of the conjugate additions. |
| Databáze: | OpenAIRE |
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