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- W4206197237 abstract "• Syntheses of both enantiomers of 5-hydroxyequol by using MacMillans’ asymmetric α-arylation protocol. • Definition of the absolute configuration of natural 5-hydroxyequol. • Synthesis of new class of equol congener 3-(4-hydroxyphenyl)chroman-8-ol as both enantio-enriched forms. 5-Hydroxyequol, a biologically active isoflavone metabolite from genistein, has been synthesized enantioselectively from 3-(2,4,6-trimethoxyphenyl)propanal by using MacMillans’ asymmetric α -arylation protocol of carbonyl compound. ( S )- and ( R )-5-Hydroxyequols have been obtained in 90% and 88% ee, respectively, by employing enantiomeric imidazolidinone catalysts derived from D- and L-phenylglycines. The absolute configuration of natural 5-hydroxyequol has been definitely assigned to ( S) -stereochemistry. ( S )- And ( R )-3-(4-hydroxyphenyl)chroman-8-ol, an unnatural equol isomer, have also been synthesized for the first time in 76% and 84% ee, respectively." @default.
- W4206197237 created "2022-01-25" @default.
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- W4206197237 date "2021-11-01" @default.
- W4206197237 modified "2023-10-03" @default.
- W4206197237 title "Easy access to both enantiomers of 5-hydroxyequol and 3-(4-hydroxyphenyl)chroman-8-ol" @default.
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- W4206197237 doi "https://doi.org/10.1016/j.rechem.2021.100252" @default.
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