Enantioselective Iron-Catalyzed Azidation of β‑Keto Esters and Oxindoles

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 enant...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-04, Vol.135 (14), p.5356-5359
Main Authors: Deng, Qing-Hai, Bleith, Tim, Wadepohl, Hubert, Gade, Lutz H
Format: Article
Language:English
Subjects:
Azides - chemical synthesis
Azides - chemistry
Catalysis
Esters - chemistry
Ferrous Compounds - chemistry
Indoles - chemistry
Ketones - chemistry
Models, Molecular
Molecular Structure
Stereoisomerism
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Summary: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%).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja402082p