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Synthesis 1994; 1994(6): 563-566
DOI: 10.1055/s-1994-25524
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Facile Synthesis of α-Hydroxy Amides and Esters by Direct Autoxidation of Their Titanium Enolates

Waldemar Adam* , Markus Metz, Frank Prechtl, Michael Renz
  • *Institute for Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany
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Publication Date:
17 September 2002 (online)

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The autoxidation of titanium enolates 2, derived from amides and esters 1, afforded either directly the corresponding α-hydroxy carbonyl compounds 3 or, by variation of the reaction conditions, the γ-hydroxy β-keto ester 4 from ester 1g in good yields (64-85 %). Unfortunately, the chiral titanium enolate 2d exhibited a low diastereoselectivity (d.r. 67: 33) for this oxygen-transfer process.

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