Chemoselective Reduction of Azlactones Using Schwartz's Reagent.

J Org Chem

Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG CEP 36036-900, Brazil.

Published: June 2017

AI Article Synopsis

  • This method uses Schwartz's reagent to selectively add to azlactones, enabling the creation of functionalized α-amino aldehydes quickly and effectively.
  • The reactions occur at room temperature and reach completion in just 2 minutes, resulting in good to high isolated yields.
  • Additionally, the process is robust, tolerating sensitive functional groups, and an excess of reagent can yield a highly functionalized allylic alcohol with an 86% yield.

Article 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.

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Source
http://dx.doi.org/10.1021/acs.joc.7b00820DOI Listing

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