Journal
TETRAHEDRON
Volume 56, Issue 43, Pages 8433-8441Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00771-7
Keywords
chemoselective hydrogenation; N-Cbz protective group; Pd/C(en) catalyst
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A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C-ethylenediamine [5% Pd/C(en)] and THF (or 1,4-dioxane) as a solvent, and the scope and limitations of this methodology were investigated. These results reinforce the utility of N-Cbz protective groups in synthetic chemistry, especially in peptide synthesis (C) 2000 Elsevier Science Ltd. All lights reserved.
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