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

J Org Chem

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

Published: May 2021

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279496PMC
http://dx.doi.org/10.1021/acs.joc.0c03055DOI Listing

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