- Enantioselective Synthesis of Isoflavanones by Catalytic Dynamic Kinetic Resolution
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A ruthenium-catalyzed asymmetric transfer hydrogenation of racemic isoflavanones with dynamic kinetic resolution yields virtually enantiopure isoflavanols as single diastereomers. Subsequent oxidation gives rise to isoflavanones in high enantiomeric purit
- Qin, Tao,Metz, Peter
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supporting information
p. 2981 - 2984
(2017/06/07)
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- SYNTHESIS OF ISOFLAVANES AND INTERMEDIATES THEREOF
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Subject of the invention is a method for enantioselective production of an isoflavane from an isoflavone, comprising the steps: (a) selectively reducing the isoflavone, such that the 4-keto group of the isoflavone is converted to a 4-hydroxy group, and the 2,3-double bond of the isoflavone is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate. The invention also relates to intermediates of formulae (IV), (V), (VI) and (VII) obtainable in the inventive process.
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Page/Page column 25
(2016/04/20)
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- Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans
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Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3·OEt2 catalyzed arylation reactions of 4′,7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4′,7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers.
- Deodhar, Mandar,Wood, Kasey,Black, David Stc,Kumar, Naresh
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p. 6697 - 6700,4
(2012/12/13)
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- Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans
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Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3·OEt2 catalyzed arylation reactions of 4′,7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4′,7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers.
- Deodhar, Mandar,Wood, Kasey,Black, David Stc,Kumar, Naresh
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p. 6697 - 6700
(2013/01/15)
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- Production of isoflavone derivatives
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Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.
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Page/Page column 13
(2008/06/13)
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- A Synthesis of Hydroxylated Isoflavylium Salts and Their Reduction Products
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Phloroglucinol reacts with arylmalondialdehydes in the presence of hydrochloric acid to form 5,7-dihydroxyisoflavylium salts.Reduction of these salts can be utilized to form isoflav-2-enes, isoflav-3-enes or isoflavans.
- Liepa, Andris J.
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p. 2647 - 2655
(2007/10/02)
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