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Synlett 1991; 1991(7): 479-480
DOI: 10.1055/s-1991-20767
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Reduction of α-Trimethylsiloxy Nitriles by Diisobutylaluminum Hydride. An Efficient and Facile Stepwise Preparation of α-Trimethylsiloxy Aldehydes and α-Hydroxy Aldehydes from Ketones

Masahiko Hayashi* , Tomoko Yoshiga, Nobuki Oguni
  • *Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 753, Japan
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Publication Date:
07 March 2002 (online)

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Reduction of α-trimethylsiloxy nitriles with diisobutylaluminum hydride (DIBAH) followed by hydrolysis of the imines formed with dilute sulfuric acid provides the corresponding α-trimethylsiloxy aldehydes in high yield. Subsequent treatment of the α-siloxy aldehydes with dilute hydrochloric acid results in the preparation of labile α-hydroxy aldehydes in good yield.