Open AccessDesymmetrization 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 -
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) - stereocenter , desymmetrization , enantioselective synthesis , chemistry , optically active , enantiomer , sulfide , halogenation , deprotonation , stereochemistry , combinatorial chemistry , organic 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.