- Rhodium-mediated asymmetric transfer hydrogenation: A diastereo- and enantioselective synthesis of: Syn -α-amido β-hydroxy esters
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The preparation of syn α-benzoylamido β-hydroxy esters through asymmetric transfer hydrogenation (ATH) with a tethered Rh(iii)-DPEN complex via dynamic kinetic resolution (DKR) has been developed for the first time starting from α-benzoylamido β-keto esters. A variety of α-benzoylamido β-keto esters were converted under mild conditions into the corresponding syn α-benzoylamino β-hydroxy esters with high yields (up to 98%) and diastereomeric ratios (up to >99:1 dr) as well as excellent enantioselectivities (up to >99% ee).
- Zheng, Long-Sheng,Férard, Charlène,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie
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supporting information
p. 283 - 286
(2018/01/12)
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- PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE BETA-HYDROXY- ALPHA-AMINOCARBOXYLIC ACID DERIVATIVES
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There is provided a process for efficiently producing an anti form of an optically active β-hydroxy-α-aminocarboxylic acid derivative that is useful as an intermediate for pharmaceuticals and agrochemicals. The process for producing optically active β-hydroxy-α-aminocarboxylic acid derivative of formula (2) or (3) wherein R1 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, R2 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, characterized by comprising subjecting an α-aminoacyl acetic acid ester compound of formula (1) wherein R1 and R2 have the same meaning as the above, to hydrogenation by catalytic asymmmetric hydrogenation in the presence of an acid.
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Page/Page column 21-22
(2010/11/08)
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- Dynamic kinetic resolution catalyzed by Ir axially chiral phosphine catalyst: Asymmetric synthesis of anti aromatic β-hydroxy-α-amino acid esters
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The anti selective hydrogenation of α-amino-β-keto esters via dynamic kinetic resolution was achieved for the first time by using the iridium-MeOBIPHEP catalyst in asymmetric synthesis of anti aromatic β-hydroxy-α-amino acid esters with excellent diastereo- and enantioslectivities. Acetic acid as a solvent and sodium acetate as an additive affected dramatically the yield and the enantioselectivity, respectively. The product anti aromatic β-hydroxy-α-amino acid esters are useful for synthesis of pharmaceuticals and natural products. Copyright
- Makino, Kazuishi,Hiroki, Yasuhiro,Hamada, Yasumasa
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p. 5784 - 5785
(2007/10/03)
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