Tetrahedron

Undesirable deprotection of O-TBDMS groups by Pd/C-catalyzed hydrogenation and chemoselective hydrogenation using a Pd/C (en) catalyst

K Hattori, H Sajiki, K Hirota

Index: Hattori, Kazuyuki; Sajiki, Hironao; Hirota, Kosaku Tetrahedron, 2001 , vol. 57, # 11 p. 2109 - 2114

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Citation Number: 59

Abstract

In general, O-TBDMS protective groups have been believed to be stable toward Pd/C- catalyzed hydrogenation conditions. In practice, however, frequent and unexpected loss of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. When a 10% Pd/C– ethylenediamine complex catalyst [10% Pd/C (en)] was used instead of 10% Pd/C, the ...