Versatile solid-phase synthesis of secondary amines from alcohols.: Development of an N-Boc-(o-nitrobenzene)sulfonamide linker

被引：9
作者：
Congreve, MS
Kay, C
Scicinski, JJ
Ley, SV
Williams, G
Murray, PJ
McKeown, SC
Watson, SP
机构：
[1] Univ Cambridge, GlaxoSmithKline, Cambridge CB2 1EW, England
[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[3] OSI Pharmaceut, Oxford OX4 6LT, England
[4] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 21期
关键词：
D O I：
10.1016/S0040-4039(03)00574-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of a versatile amine releasing linker based on the modified o-nitrobenzene sulfonamide protective group is described. This new N-Boc-o-nitrobenzenesulfonamide (Boc-ONBS) linker enables the elaboration on resin of primary and secondary amines by sequential substitution of the sulfonamide moiety using the Mitsunobu reaction. A 16-member array of secondary and Boc protected primary amines was then prepared using this linker. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4153 / 4156
页数：4
相关论文
共 13 条
[1]  
BYCROFT BW, 1993, CHEM COMMUN, P778
[2]  
CHEUNG M, 1996, 211 ACS M NEW ORL MA
[3]  
Fukuyama T, 1999, SYNLETT, P1301
[4]   2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES [J].
FUKUYAMA, T ;
JOW, CK ;
CHEUNG, M .
TETRAHEDRON LETTERS, 1995, 36 (36) :6373-6374
[5]   Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry [J].
Guillier, F ;
Orain, D ;
Bradley, M .
CHEMICAL REVIEWS, 2000, 100 (06) :2091-2157
[6]   Linkers for solid phase organic synthesis [J].
James, IW .
TETRAHEDRON, 1999, 55 (16) :4855-4946
[7]   A novel, chemically robust, amine releasing linker [J].
Kay, C ;
Murray, PJ ;
Sandow, L ;
Holmes, AB .
TETRAHEDRON LETTERS, 1997, 38 (39) :6941-6944
[8]   A photolabile carbamate based dual linker analytical construct for facile monitoring of solid phase chemistry: 'TLC' for solid phase? [J].
McKeown, SC ;
Watson, SP ;
Carr, RAE ;
Marshall, P .
TETRAHEDRON LETTERS, 1999, 40 (12) :2407-2410
[9]   Rapid reaction scanning of solid phase chemistry using resins incorporating analytical constructs [J].
Murray, PJ ;
Kay, C ;
Scicinski, JJ ;
McKeown, SC ;
Watson, SP ;
Carr, RAE .
TETRAHEDRON LETTERS, 1999, 40 (30) :5609-5612
[10]   Dde - A selective primary amine protecting group: A facile solid phase synthetic approach to polyamine conjugates [J].
Nash, IA ;
Bycroft, BW ;
Chan, WC .
TETRAHEDRON LETTERS, 1996, 37 (15) :2625-2628
12