Facile and efficient addition of terminal alkynes to benzotriazole esters: synthesis of d-erythro-sphingosine using ynones as the key intermediate

JA Morales-Serna, A Sauza, GP de Jesús, R Gaviño…

Index: Morales-Serna, Jose Antonio; Sauza, Alejandro; Padron De Jesus, Gabriela; Gavino, Ruben; Garcia De La Mora, Gustavo; Cardenas, Jorge Tetrahedron Letters, 2013 , vol. 54, # 52 p. 7111 - 7114

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Citation Number: 6

Abstract

Abstract From the perspective of synthesis, ynones are compounds of considerable interest because of their occurrence in a wide variety of biologically active molecules and as key synthetic intermediates. In this context, a facile and highly efficient synthesis of ynones was developed based on the high reactivity of benzotriazole esters formed in situ. Lithium acetylides can alkylate various carboxylic acids in yields ranging from 60% to 92%. To ...