Reaktionen von aluminiumalkylen mit carbonyl-verbindungen: II. Hydroaluminierung von aldoenolestern—eine Neue 1,3-diolsynthese

Add time:09/24/2019    Source:sciencedirect.com

Under moderate conditions aldoenol esters react with HAl(i-C4H9)2 to afford organoaluminium compounds, which upon hydrolysis yield 1,3-diols and on acetolysis form 1,3-diacetates. The diacetates are obtained in about 50% yields (based on enol ester) by distillation. Vinyl esters are converted to linear 1,3-diols or 1,3-diacetates, whereas enol acetates of higher aldehydes give 2-sec(or -tert)alkyl-1,3-butanediols or 2-sec(or -tert)alkyl-1,3-butanediol diacetates.

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