The Journal of Organic Chemistry 2017-05-11

Chemoselective Reduction of Azlactones Using Schwartz’s Reagent

Danielle L. J. Pinheiro, Eloah P. Ávila, Gabriel M. F. Batista, Giovanni W. Amarante

Index: 10.1021/acs.joc.7b00820

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Abstract

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.