The undesirable lability of tert-butyldimethylsilyl ethers under Pd/C-catalyzed hydrogenation conditions and solution of the problem by using a Pd/C(en) catalyst

被引:51
作者
Hattori, K [1 ]
Sajiki, H [1 ]
Hirota, K [1 ]
机构
[1] Gifu Pharmaceut Univ, Med Chem Lab, Gifu 5025858, Japan
关键词
TBDMS ethers; desilylation; Pd/C; Pd/C(en); chemoselective hydrogenation;
D O I
10.1016/S0040-4039(00)00935-7
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
While the frequent and unexpected loss of the TBDMS protective group of a variety of hydroxylic functions was demonstrated under neutral and mild hydrogenation conditions using 10% Pd/C, the undesirable problem was perfectly overcome by using a 10% Pd/C-ethylenediamine complex catalyst. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5711 / 5714
页数:4
相关论文
共 15 条
[1]
PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[2]
SELECTIVITY IN THE CATALYTIC TRANSFER HYDROGENOLYSIS OF SILYL ETHER PROTECTING GROUPS [J].
CORMIER, JF ;
ISAAC, MB ;
CHEN, LF .
TETRAHEDRON LETTERS, 1993, 34 (02) :243-246
[3]
Cleavage of tert-butyldimethylsilyl ethers by chloride ion [J].
Farràs, J ;
Serra, C ;
Vilarrasa, J .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :327-330
[4]
Greene T. W., 1999, PROTECTIVE GROUPS OR, P113
[5]
Selective deprotection of alkyl t-butyldimethylsilyl ethers in the presence of aryl t-butyldimethylsilyl ethers [J].
Grieco, PA ;
Markworth, CJ .
TETRAHEDRON LETTERS, 1999, 40 (04) :665-666
[6]
One-step conversion of formate esters to O-silyl ethers by means of samarium diiodide in the presence of chlorosilane reagents [J].
Honda, T ;
Ishikawa, F .
SYNTHETIC COMMUNICATIONS, 1999, 29 (19) :3323-3328
[7]
Selective acceleration for deprotection of benzyl ethers with Ti-HMS [J].
Itoh, A ;
Kodama, T ;
Maeda, S ;
Masaki, Y .
TETRAHEDRON LETTERS, 1998, 39 (51) :9461-9464
[8]
KOCIENSKI PJ, 1994, PROTECTING GROUPS, P28
[9]
A SIMPLE AND HIGHLY CHEMOSELECTIVE DESILYLATION TERT-BUTYLDIMETHYLSILYL ETHERS [J].
LEE, ASY ;
YEH, HC ;
TSAI, MH .
TETRAHEDRON LETTERS, 1995, 36 (38) :6891-6894
[10]
Selective deprotection of alkyl vs. aryl silyl ethers [J].
Lipshutz, BH ;
Keith, J .
TETRAHEDRON LETTERS, 1998, 39 (17) :2495-2498