Tetrahedron

Click à la carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions

IE Valverde, AF Delmas, V Aucagne

Index: Valverde, Ibai E.; Delmas, Agnes F.; Aucagne, Vincent Tetrahedron, 2009 , vol. 65, # 36 p. 7597 - 7602

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Citation Number: 51

Abstract

We herein describe an in-depth screening and systematic comparison of five classical silyl alkyne protective groups, to evaluate their potential in the context of multiple successive copper (I)-catalyzed alkyne–azide cycloadditions (CuAAC). We confirm the relative sensitivity of TMS, especially under CuAAC conditions. The relative robustness of its higher analogues, and the discovery of mild silver-catalyzed deprotection conditions selective for ...