Tetrahedron Letters p. 5059 - 5062 (1999)
Update date:2022-08-04
Topics:
Kanemasa, Shuji
Araki, Takahiro
Kanai, Toshio
Wada, Eiji
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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