A novel, thioacetal based linker for solid-phase synthesis

被引:32
作者
Huwe, CM [1 ]
Künzer, H [1 ]
机构
[1] Schering AG, Preclin Drug Res, D-13342 Berlin, Germany
关键词
combinatorial chemistry; solid-phase synthesis; thioacetals;
D O I
10.1016/S0040-4039(98)02580-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Commercially available (+/-)-alpha-lipoic acid was employed as a novel, chemically robust linker for the immobilization of ketones. The utility of this thioacetal based linker in solid-phase synthesis was demonstrated by synthesizing several 4-acetylbiphenyls and 4-alkoxyacetophenones via Suzuki and Mitsunobu reactions, respectively. The products were easily cleaved from solid support by treatment with [bis(trifluoroacetoxy)iodo] benzene. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:683 / 686
页数:4
相关论文
共 26 条
[1]  
[Anonymous], ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANIE.199622881
[2]   CARBON-CARBON BOND-FORMING METHODS ON SOLID SUPPORT - UTILIZATION OF KENNER SAFETY-CATCH LINKER [J].
BACKES, BJ ;
ELLMAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11171-11172
[3]  
Balkenhohl F., 1996, ANGEW CHEM, V108, P2436
[4]   Arylsulfonate esters in solid phase organic synthesis. II. Compatibility with commonly-used reaction conditions [J].
Baxter, EW ;
Rueter, JK ;
Nortey, SO ;
Reitz, AB .
TETRAHEDRON LETTERS, 1998, 39 (09) :979-982
[5]   PhFl polystyrene: A new resin for solid phase organic synthesis [J].
Bleicher, KH ;
Wareing, JR .
TETRAHEDRON LETTERS, 1998, 39 (26) :4587-4590
[6]  
BURGESS K, 1997, J CHEM SOC CHEM COMM, P785
[7]   The Suzuki-Miyaura cross coupling reactions on solid support.: Link to solution phase directed ortho metalation.: The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes [J].
Chamoin, S ;
Houldsworth, S ;
Kruse, CG ;
Bakker, WI ;
Snieckus, V .
TETRAHEDRON LETTERS, 1998, 39 (24) :4179-4182
[8]  
Dankwardt SM, 1997, SYNLETT, P854
[9]   Solid phase synthesis of 2-substituted benzofurans via the palladium-catalysed heteroannulation of acetylenes [J].
Fancelli, D ;
Fagnola, MC ;
Severino, D ;
Bedeschi, A .
TETRAHEDRON LETTERS, 1997, 38 (13) :2311-2314
[10]  
Fruchtel J. S., 1996, ANGEW CHEM, V108, P19