Fluoride-catalyzed aldol reaction of ethyl trimethylsilyldiazoacetate with aldehydes leading to ethyl α-diazo-β-hydroxy esters and rhodium catalyzed decarboxylative rearrangement of diazo urethanes leading to β-amino acrylates

Add time:07/11/2019    Source:sciencedirect.com

Ethyl trimethylsilyldiazoacetate reacts smoothly with a variety of aldehydes at 0 °C in the presence of a catalytic amount of tetrabutylammonium fluoride to produce α-diazo-β-hydroxy esters in good to excellent yields. The resulting α-diazo-β-hydroxy esters can be stereoselectively transformed, by a sequence of carbamation with p-toluenesulfonyl isocyanate and rhodium(II)-induced decarboxylative rearrangement, to α- or β-substituted β-(p-toluenesulfonylamino)acrylates depending upon migration aptitude of the substituents derived from the aldehydes.

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