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Asymmetric Electrophilic Reactions in Phosphorus Chemistry

V.P. Kukhar’ Institute of Bioorganic Chemistry and Petrochemistry, NAS of Ukraine, Murmanska st., 1, 02094 Kyiv, Ukraine
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Symmetry 2020, 12(1), 108; https://doi.org/10.3390/sym12010108 (registering DOI)
Received: 16 November 2019 / Revised: 8 December 2019 / Accepted: 27 December 2019 / Published: 6 January 2020
This review is devoted to the theoretic and synthetic aspects of asymmetric electrophilic substitution reactions at the stereogenic phosphorus center. The stereochemistry and mechanisms of electrophilic reactions are discussed—the substitution, addition and addition-elimination of many important reactions. The reactions of bimolecular electrophilic substitution SE2(P) proceed stereospecifically with the retention of absolute configuration at the phosphorus center, in contrast to the reactions of bimolecular nucleophilic substitution SN2(P), proceeding with inversion of absolute configuration. This conclusion was made based on stereochemical analysis of a wide range of trivalent phosphorus reactions with typical electrophiles and investigation of examples of a sizeable number of diverse compounds. The combination of stereospecific electrophilic reactions and stereoselective nucleophilic reactions is useful and promising for the further development of organophosphorus chemistry. The study of phosphoryl group transfer reactions is important for biological and molecular chemistry, as well as in studying mechanisms of chemical processes involving organophosphorus compounds. New versions of asymmetric electrophilic reactions applicable for the synthesis of enantiopure P-chiral secondary and tertiary phosphines are discussed. View Full-Text
Keywords: electrophilic reactions; stereochemistry of organophosphorus compounds; stereospecificity electrophilic reactions; stereochemistry of organophosphorus compounds; stereospecificity
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Kolodiazhna, A.O.; Kolodiazhnyi, O.I. Asymmetric Electrophilic Reactions in Phosphorus Chemistry. Symmetry 2020, 12, 108.

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