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

Elżbieta Łastawiecka | Zendy; Sławomir Frynas | Zendy; K. Michał Pietrusiewicz | Zendy

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

Author(s) -

Elżbieta Łastawiecka,

Sławomir Frynas,

K. Michał Pietrusiewicz

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c03055

Subject(s) - chemistry , stereocenter , desymmetrization , enantioselective synthesis , optically active , halogenation , sulfide , enantiomer , deprotonation , stereochemistry , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , ion

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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