Tetrahedron letters

Homologation of α-hydroxy acids to α-unsubstituted β-hydroxy carboxamides via Arndt–Eistert reaction

J Spengler, J Ruíz-Rodríguez, K Burger, F Albericio

Index: Spengler, Jan; Ruiz-Rodriguez, Javier; Burger, Klaus; Albericio, Fernando Tetrahedron Letters, 2006 , vol. 47, # 27 p. 4557 - 4560

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Citation Number: 6

Abstract

Here we studied the homologation of leucic and phenyl lactic acid via Wolff-rearrangement of their diazoketones to the corresponding β-hydroxy acids. This reaction requires distinct conditions to that of their amino acid analogues. The choice of the Oα-substituent can selectively direct the reaction to α-unsubstituted β-hydroxy carboxamides or (E)-α, β- unsaturated carboxamides and offers a new route from α-hydroxy acids to such ...