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

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 TES compared to DPS or TIPS allowed us to design a strategy allowing three successive CuAAC on a single scaffold, as we have illustrated by the synthesis of a tris-triazolo model compound.
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https://hal.archives-ouvertes.fr/hal-00525398
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Submitted on : Monday, October 11, 2010 - 5:11:59 PM
Last modification on : Tuesday, June 4, 2019 - 4:30:10 PM

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Ibai E. Valverde, Agnès F. Delmas, Vincent Aucagne. Click a la carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions. Tetrahedron, Elsevier, 2009, 65 (36), pp.7597-7602. ⟨10.1016/j.tet.2009.06.093⟩. ⟨hal-00525398⟩

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