- Highly Diastereo- and Enantioselective Access to syn-α-Amido β-Hydroxy Esters via Ruthenium-Catalyzed Dynamic Kinetic Resolution-Asymmetric Hydrogenation
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Dynamic kinetic resolution (DKR) of racemic aryl α-amino β-ketoesters via Ru-diphosphine-catalyzed asymmetric hydrogenation was realized at 70 °C under 50 atm of hydrogen, affording syn α-amido β-hydroxy esters in high yields (up to 96%) with high reactivity (TON up to 940) and diastereo- and enantioselectivities (up to 99:1 dr, 98% ee). These hydrogenation products provide valuable chiral synthons in many natural products and pharmaceuticals. Gram-scale DKR asymmetric hydrogenation (DKR-AH) was also performed with retained reactivity and stereoselectivity, revealing the synthetic utility of this method.
- Lu, Bin,Wu, Xiaoyu,Li, Chengyang,Ding, Guangni,Li, Wanfang,Xie, Xiaomin,Zhang, Zhaoguo
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p. 3201 - 3213
(2019/03/11)
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- Peptide inhibitors of CDK2-cyclin A that target the cyclin recruitment-Site: Structural variants of the C-Terminal Phe
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A focused series of octapeptides based on the lead compound H-His-Ala-Lys-Arg-Arg-Leu-Ile-Phe-NH2 1, in which the C-terminal phenylalanine residue was replaced by α and/or β-modified variants, was synthesized using solid-phase chemistry. Both the L-threo-β-hydroxy-phenylalanine (β-phenylserine, Pse) and (2S)-phenylalaninol derivatives, as competitive binders at the cyclin-recruitment site, displayed potent inhibitory activity towards the CDK2-cyclin A complex. Unexpectedly, the D-threo-Pse derivatives also showed inhibitory activity.
- Atkinson, Gail E.,Cowan, Angela,McInnes, Campbell,Zheleva, Daniella I.,Fischer, Peter M.,Chan, Weng C.
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p. 2501 - 2505
(2007/10/03)
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- Asymmetric synthesis of syn hydroxyphenylalanine via aziridine ring expansion to an oxazoline
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The synthesis of (2R,3S)- and (2S,3R)-hydroxyphenylalanine is reported. The main steps are the 1,4-addition of O-benzylhydroxylamine to unsaturated imides and the ring expansion of trans-aziridines.
- Cardillo, Giuliana,Gentilucci, Luca,Tolomelli, Alessandra
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p. 8261 - 8264
(2007/10/03)
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- Resolution of β-hydroxy-α-amino acids by the action of proteases on their N-acyl methyl esters
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Methyl N-acetyl phenylserinates (1, 2), methyl N-acetyl nitrophenylserinates (3, 4), and methyl N-benzoyl threoninates (5, 6) were resolved conveniently into the enantiomers with high optical purities by enzymatic hydrolysis in the presence of α-chymotryp
- Chenevert, Robert,Letourneau, Martin,Thiboutot, Sonia
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p. 960 - 963
(2007/10/02)
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