Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones

Elżbieta Łastawiecka; Sławomir Frynas; K Michał Pietrusiewicz

doi:10.1021/acs.joc.0c03055

Desymmetrization Approach to the Synthesis of Optically Active P-Stereogenic Phosphin-2-en-4-ones

J Org Chem. 2021 May 7;86(9):6195-6206. doi: 10.1021/acs.joc.0c03055. Epub 2021 Apr 26.

Authors

Elżbieta Łastawiecka¹, Sławomir Frynas¹, K Michał Pietrusiewicz¹

Affiliation

¹ Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Marie Curie-Sklodowska University, Gliniana 33 St., 20-614 Lublin, Poland.

Abstract

Two synthetic protocols for the conversion of 1-phenylphosphinan-4-ones to novel P-stereogenic 1-phenylphosphin-2-en-4-ones by enantioselective deprotonation followed by oxidation and by asymmetric organocatalytic halogenation accompanied by elimination have been developed. These two-step one-pot transformations provide convenient access to optically active 1-phenylphosphin-2-en-4-one 1-sulfide and 1-phenylphosphin-2-en-4-one 1-oxide of 96 and 55% enantiomeric purities, respectively.