Chiral Synthetic Equivalents of 2-Cyanoethyl Tetraisopropylphosphorodiamidite: Application to the Synthesis and Resolution of Chiral Phosphoric Acids

Autor:	Pascal Retailleau, Angela Marinetti, Jérémie Stemper, Jean-François Betzer, Kévin Isaac
Rok vydání:	2014
Předmět:	Chiral column chromatography Resolution (mass spectrometry) Chemistry Organic Chemistry Diastereomer Organic chemistry Fractional crystallization (chemistry) Physical and Theoretical Chemistry Chiral derivatizing agent
Zdroj:	European Journal of Organic Chemistry. 2014:4099-4106
ISSN:	1434-193X
Popis:	Four synthetic equivalents of (iPr2N)2P-OCH2CH2CN (1) have been prepared from readily available enantiomerically pure β-hydroxynitriles as well as from chiral β-hydroxy esters. To demonstrate their possible use as phosphinating/resolving agents, these phosphorodiamidites have been used in the synthesis of known phosphoric acids. The method allows enantiomerically pure acids to be obtained through separation of the diastereomeric phosphates. The method should favorably compete with other resolution procedures, e.g. fractional crystallization or chiral HPLC, for the small-scale synthesis of new phosphoric acids for screening purposes. As synthetic equivalents of 1, these auxiliaries might find applications also in other areas, for the synthesis of biologically relevant compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8c21694a25f977bbed0cc6b3c36f525e https://doi.org/10.1002/ejoc.201402203 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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