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Chiral Synthetic Equivalents of 2‐Cyanoethyl Tetraisopropylphosphorodiamidite: Application to the Synthesis and Resolution of Chiral Phosphoric Acids
Author(s) -
Isaac Kévin,
Stemper Jérémie,
Retailleau Pascal,
Betzer JeanFrançois,
Marinetti Angela
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402203
Subject(s) - diastereomer , resolution (logic) , phosphoric acid , chemistry , combinatorial chemistry , fractional crystallization (geology) , chiral resolution , organic chemistry , enantiomer , biology , computer science , artificial intelligence , basalt , paleontology
Four synthetic equivalents of ( i Pr 2 N) 2 P‐OCH 2 CH 2 CN ( 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.