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.
Moliterno, M., Margarita, C., Panarello, S., Salvio, R., Bella, M. (2014). Synthesis of 1,2-Diols and Their Base-Initiated Rearrangement to Butyrolactones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014(31), 6896-6902 [10.1002/ejoc.201402853].
Synthesis of 1,2-Diols and Their Base-Initiated Rearrangement to Butyrolactones
Salvio R.;
2014-01-01
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 | Dimensione | Formato | |
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