Enantioselective Synthesis ofanti-β-Hydroxy-α-amido Esters via Transfer Hydrogenation
- 21 October 2010
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (22) , 5274-5277
Abstract
The asymmetric transfer hydrogenation of α-amido-β-keto esters to provide the corresponding anti-β-hydroxy-α-amido esters in good to excellent yields, diastereoselectivity, and enantioselectivity is reported. The procedure is operationally simple, and delicate handling of the catalyst is not necessary.Keywords
This publication has 45 references indexed in Scilit:
- Highly Diastereo- and Enantioselective Synthesis of Monodifferentiated syn-1,2-Diol Derivatives through Asymmetric Transfer Hydrogenation via Dynamic Kinetic ResolutionOrganic Letters, 2010
- Total Synthesis of (−)-Muraymycin D2 and Its EpimerThe Journal of Organic Chemistry, 2010
- Dynamic Kinetic Resolution: Asymmetric Transfer Hydrogenation of α-Alkyl-Substituted β-KetoamidesOrganic Letters, 2009
- Catalytic asymmetric hydrogenation of α-amino-β-keto ester hydrochlorides using homogeneous chiral nickel-bisphosphine complexes through DKRChemical Communications, 2008
- Bifunctional transition metal-based molecular catalysts for asymmetric synthesesOrganic & Biomolecular Chemistry, 2005
- Catalytic Enantio- and Diastereoselective Aldol Reactions of Glycine-Derived Silicon Enolate with Aldehydes: An Efficient Approach to the Asymmetric Synthesis of anti-β-Hydroxy-α-Amino Acid DerivativesJournal of the American Chemical Society, 2004
- A Versatile Route to syn‐ and anti‐α‐Amino β‐Hydroxy Esters from β‐Keto Esters by Dynamic Kinetic Resolution with Ru‐SYNPHOS® CatalystEuropean Journal of Organic Chemistry, 2004
- Dynamic kinetic resolution: an efficient route to anti α-amino-β-hydroxy esters via Ru-SYNPHOS®catalyzed hydrogenationChemical Communications, 2004
- (β-Amino alcohol)(arene)ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Functionalized Ketones − Scope, Isolation of the Catalytic Intermediates, and Deactivation ProcessesEuropean Journal of Organic Chemistry, 2000
- A Novel BF3.cntdot.OEt2-Catalyzed [3 + 2] Annulation of N-Cbz-.alpha.-Amino Aldehydes with Allyltrimethylsilane. Highly Stereoselective Synthesis of Cis-2,3,5-Trisubstituted PyrrolidinesThe Journal of Organic Chemistry, 1994