1,2-Diols 3 have been synthesized by the aldol addition of hydroxy esters 1 to propargyl aldehydes 2 in dichloromethane. These 1,2-diols undergo a base-initiated rearrangement under mild conditions in methanol with an unusual 1,2-alkyl shift to afford interesting alpha,beta-unsaturated gamma-butyrolactones 4. A possible mechanism is postulated on the basis of experimental evidence and the results of DFT calculations.
Synthesis of 1,2-Diols and Their Base-Initiated Rearrangement to Butyrolactones
R Salvio;
2014
Abstract
1,2-Diols 3 have been synthesized by the aldol addition of hydroxy esters 1 to propargyl aldehydes 2 in dichloromethane. These 1,2-diols undergo a base-initiated rearrangement under mild conditions in methanol with an unusual 1,2-alkyl shift to afford interesting alpha,beta-unsaturated gamma-butyrolactones 4. A possible mechanism is postulated on the basis of experimental evidence and the results of DFT calculations.File in questo prodotto:
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