Unknown

Dataset Information

0

Asymmetric synthesis of anti-?-amino-?-hydroxy esters via dynamic kinetic resolution of ?-amino-?-keto esters.

ABSTRACT: A method for the asymmetric synthesis of enantioenriched anti-?-hydroxy-?-amino acid derivatives by enantioconvergent reduction of the corresponding racemic ?-keto esters is presented. The requisite ?-keto esters are prepared via Mannich addition of ethyl diazoacetate to imines followed by oxidation of the diazo group with Oxone. Implementation of a recently developed dynamic kinetic resolution of ?-substituted-?-keto esters via Ru(II)-catalyzed asymmetric transfer hydrogenation provides the title motif in routinely high diastereo- and enantioselectivity.

SUBMITTER: Goodman CG 

PROVIDER: S-EPMC3766400 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Asymmetric synthesis of anti-β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters.

Goodman C Guy CG   Do Dung T DT   Johnson Jeffrey S JS  

Organic letters 20130430 10

A method for the asymmetric synthesis of enantioenriched anti-α-hydroxy-β-amino acid derivatives by enantioconvergent reduction of the corresponding racemic α-keto esters is presented. The requisite α-keto esters are prepared via Mannich addition of ethyl diazoacetate to imines followed by oxidation of the diazo group with Oxone. Implementation of a recently developed dynamic kinetic resolution of β-substituted-α-keto esters via Ru(II)-catalyzed asymmetric transfer hydrogenation provides the tit  ...[more]

Similar Datasets

Unknown Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of ?-keto esters.
| S-EPMC3533366 | biostudies-literature
Unknown Dynamic kinetic resolution of ?-keto esters via asymmetric transfer hydrogenation.
| S-EPMC3342478 | biostudies-other
Unknown Dynamic kinetic asymmetric cross-benzoin additions of ?-stereogenic ?-keto esters.
| S-EPMC4210110 | biostudies-literature
Unknown Synthesis of Functionalized δ-Hydroxy-β-keto Esters and Evaluation of Their Anti-inflammatory Properties.
| S-EPMC9314795 | biostudies-literature
Unknown Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary ?-Hydroxy Esters.
| S-EPMC7540711 | biostudies-literature
Unknown Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters.
| S-EPMC8359131 | biostudies-literature
Transcriptomics Asymmetric Synthesis of Flavanols via Cu-Catalyzed Kinetic Resolution of Chromenes and Their Anti-Inflammatory Activity
2021-07-30 | GSE181052 | GEO
Unknown Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters.
| S-EPMC2669707 | biostudies-literature
Unknown Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters.
| S-EPMC3650467 | biostudies-literature
Unknown Asymmetric Mannich synthesis of ?-amino esters by anion-binding catalysis.
| S-EPMC4183616 | biostudies-literature