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

被引:56
作者
Hattori, K [1 ]
Sajiki, H [1 ]
Hirota, K [1 ]
机构
[1] Gifu Pharmaceut Univ, Med Chem Lab, Gifu 5028585, Japan
关键词
TBDMS ethers; desilylation; Pd/C; Pd/C(en); chemoselective hydrogenation;
D O I
10.1016/S0040-4020(01)00060-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 undesirable problem was perfectly overcome and the chemoselective hydrogenation of reducible functionalities leaving intact the TBDMS protective group was achieved. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2109 / 2114
页数:6
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