Chemoselective Reduction of Azlactones Using Schwartz’s Reagent

Highly chemoselective addition of Schwartz’s reagent to widely available azlactones is described. This method allows the preparation of challenged functionalized α-amino aldehydes, in good to high isolated yields at room temperature, after only 2 min reaction. The presence of sensitive functionaliti...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-06, Vol.82 (11), p.5981-5985
Main Authors: Pinheiro, Danielle L. J, Ávila, Eloah P, Batista, Gabriel M. F, Amarante, Giovanni W
Format: Article
Language:English
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Summary:Highly chemoselective addition of Schwartz’s reagent to widely available azlactones is described. This method allows the preparation of challenged functionalized α-amino aldehydes, in good to high isolated yields at room temperature, after only 2 min reaction. The presence of sensitive functionalities or electronic factors does not compromise the potential of the method. The use of an excess of the reducing reagent gave a very functionalized allylic alcohol derivative in 86% yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00820