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Synthesis of α-hydroxy carboxylic acids, esters and amides

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Recent Literature

Use of a masked acyl cyanide (MAC) reagent bearing a tert-butyldimethylsilyl group allows the synthesis of α-siloxy esters via a one-pot reaction with various aldehydes and alcohols.
H. Nemoto, R. Ma, T. Kawamura, K. Yatsuzuka, M. Kamiya, M. Shibuya, Synthesis, 2008, 3819-3827.

α-Acetoxy esters or amides were synthesized directly and in one portion from aldehydes and alcohols or amines by one-carbon homologation using a masked acyl cyanide reagent bearing an acetyl group.
H. Nemoto, T. Kawamura, K. Kitasaki, K. Yatsuzuka, M. Kamiya, Y. Yoshioka, Synthesis, 2009, 1694-1702.

A one-pot method allows the synthesis of α-siloxy-Weinreb amides from aldehydes using N,O-dimethylhydroxylamine and a masked acyl cyanide reagent bearing a tert-butyldimethylsilyl group. The TBS group avoids the competitive reaction toward N-methoxy-N-methyl-2-amino-1-siloxymalononitrile.
H. Nemoto, R. Ma, H. Moriguchi, T. Kawamura, M. Kamiya, M. Shibuya, J. Org. Chem., 2007, 72, 9850-9853.