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Stereoselective Synthesis of Highly Functionalized α-Diazo-β-ketoalkanoates via Catalytic One-Pot Mukaiyama-Aldol Reactions

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journal contribution
posted on 19.02.2010, 00:00 by Lei Zhou, Michael P. Doyle
Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce δ-siloxy-α-diazo-β-ketoalkanoates in good yield, and δ-hydroxy-α-diazo-β-ketoalkanoates are formed with high diastereoselectivity in reactions with α-diazo-β-ketopentanoate promoted by dibutylboron triflate.