Phenol-Derived Chiral Auxiliaries as Substrates in the Synthesis of Optically Active Phosphonic Acid Derivatives: Synthetic and Structural Aspects

Józef DrabowiczDepartment of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90 – 363 Łódź, Sienkiewicza 112, Poland;Institute of Chemistry, Environmental Protection and Biotechnology, Jan Dlugosz University in Częstochowa, al. Armii Krajowej 13/15, 42-200 Częstochowa, PolandCorrespondence[email protected]

Dorota KrasowskaDepartment of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90 – 363 Łódź, Sienkiewicza 112, Poland

Andrzej ŁopusińskiDepartment of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90 – 363 Łódź, Sienkiewicza 112, Poland

Anna AftykaDepartment of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90 – 363 Łódź, Sienkiewicza 112, Poland

Patrycja Pokora-SobczakDepartment of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90 – 363 Łódź, Sienkiewicza 112, Poland

Małgorzata UrbaniakDepartment of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90 – 363 Łódź, Sienkiewicza 112, Poland

Małgorzata SzyrejInstitute of Chemistry, Environmental Protection and Biotechnology, Jan Dlugosz University in Częstochowa, al. Armii Krajowej 13/15, 42-200 Częstochowa, Poland

Wanda WieczorekInstitute of Chemistry, Environmental Protection and Biotechnology, Jan Dlugosz University in Częstochowa, al. Armii Krajowej 13/15, 42-200 Częstochowa, Poland

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GRAPHICAL ABSTRACT

Abstract

Preparation of chiral phosphonic acid amidoesters or diesters derived from diastereomerically pure 1-[α-N-1-phenylethylamino]benzyl-2-naphthol or 2,2′-dihydroxy-1,1′-binaphthyl are reported. The attempted ring opening reactions of the isolated compounds with a few nucleophiles are also discussed. Basic structural data for phenyl amidophosphonate and phenylamidothiophosphonate derived from diastereomerically pure 1-[α-N-1-phenylethylamino]benzyl-2-naphthol based on X-ray structural analysis are also presented.

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Phenol-Derived Chiral Auxiliaries as Substrates in the Synthesis of Optically Active Phosphonic Acid Derivatives: Synthetic and Structural Aspects

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Phenol-Derived Chiral Auxiliaries as Substrates in the Synthesis of Optically Active Phosphonic Acid Derivatives: Synthetic and Structural Aspects

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