Enantioselective Iron-Catalyzed Azidation of β-Keto Esters and Oxindoles
Authors:
- 28 March 2013
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 135 (14) , 5356-5359
Abstract
The first example of Fe-catalyzed enantioselective azidations of β-keto esters and oxindoles using a readily available N3-transfer reagent is reported. A number of α-azido-β-keto esters were obtained with up to 93% ee, and this methodology also generates 3-substitued 3-azidooxindoles with high enantioselectivities (up to 94%).Keywords
This publication has 96 references indexed in Scilit:
- Organocatalytic Asymmetric α‐Amination of Unprotected 3‐Aryl and 3‐Aliphatic Substituted Oxindoles using Di‐tert‐butyl AzodicarboxylateAdvanced Synthesis & Catalysis, 2011
- Regenerative Biomaterials that “Click”: Simple, Aqueous-Based Protocols for Hydrogel Synthesis, Surface Immobilization, and 3D PatterningBioconjugate Chemistry, 2011
- Reliable and Efficient Procedures for the Conjugation of Biomolecules through Huisgen Azide–Alkyne CycloadditionsAngewandte Chemie International Edition, 2011
- Bioorthogonal Labeling of 5-Hydroxymethylcytosine in Genomic DNA and Diazirine-Based DNA Photo-Cross-Linking ProbesAccounts of Chemical Research, 2011
- Perfluorophenyl Azides: New Applications in Surface Functionalization and Nanomaterial SynthesisAccounts of Chemical Research, 2010
- Cu(I)-Catalyzed Huisgen Azide−Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide ChemistryChemical Reviews, 2009
- AG-041R, a Gastrin/CCK-B Antagonist, Stimulates Chondrocyte Proliferation and Metabolism in VitroBiochemical and Biophysical Research Communications, 2001
- Efficient Synthesis of (R)-4-((Trimethylsilyl)oxy)-2-cyclopentenone by Enantioselective Catalytic Epoxide Ring OpeningThe Journal of Organic Chemistry, 1996
- Preparation of Novel Cyclic Hypervalent Idoine(III) Compounds Having Azido, Cyano, and Nitrato LigandsHETEROCYCLES, 1996
- Synthesis and thermolysis of 3-azidoindolenines.Chemical and Pharmaceutical Bulletin, 1978