A novel route to functionalized PFP esters via rapid intermolecular radical addition to PFP acrylate mediated by ethylpiperidinium hypophosphite (EPHP)

被引:13
作者
Caddick, S
Hamza, D
Judd, DB
Reich, MT
Wadman, SN
Wilden, JD
机构
[1] UCL, Dept Chem, London WC1H 0AJ, England
[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England
[3] Univ Sussex, Ctr Mol Design & Drug Dev, Brighton BN1 9QJ, E Sussex, England
[4] GlaxoSmithKline, High Throughput Chem, Stevenage SG1 2NY, Herts, England
基金
英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会;
关键词
EPHP; radical; addition; amides; PFP esters;
D O I
10.1016/j.tetlet.2004.01.082
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pentafluorophenyl (PFP) acrylate, a stable compact bifunctional scaffold undergoes rapid N-ethylpiperidinium hypophosphite (EPHP) mediated conjugate radical addition to yield a variety of active esters susceptible to further functionalization by aminolysis. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:2363 / 2366
页数:4
相关论文
共 36 条
[1]   APPLICATIONS OF RADICAL-ADDITION REACTIONS TO THE SYNTHESIS OF A C-GLUCOSIDE AND A FUNCTIONALIZED AMINO-ACID [J].
ADLINGTON, RM ;
BALDWIN, JE ;
BASAK, A ;
KOZYROD, RP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :944-945
[2]  
Albericio F, 1997, METHOD ENZYMOL, V289, P104
[3]  
[Anonymous], 2001, Radicals in Organic Syntheses
[4]   SOLID-PHASE PEPTIDE-SYNTHESIS USING N-ALPHA-FLUORENYLMETHOXYCARBONYLAMINO ACID PENTAFLUOROPHENYL ESTERS [J].
ATHERTON, E ;
SHEPPARD, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (03) :165-166
[5]   Formation of monomeric halogenoaryl acrylates in the presence of hindered pyridine bases [J].
Blazejewski, JC ;
Hofstraat, JW ;
Lequesne, C ;
Wakselman, C ;
Wiersum, UE .
JOURNAL OF FLUORINE CHEMISTRY, 1998, 91 (02) :175-177
[6]   Solid-phase intermolecular radical reactions 2:: Synthesis of C-glycopeptide mimetics via a novel acrylate acceptor [J].
Caddick, S ;
Hamza, D ;
Wadman, SN ;
Wilden, JD .
ORGANIC LETTERS, 2002, 4 (10) :1775-1777
[7]   A new route to sulfonamides via intermolecular radical addition to pentafluorophenyl vinylsulfonate and subsequent aminolysis [J].
Caddick, S ;
Wilden, JD ;
Bush, HD ;
Wadman, SN ;
Judd, DB .
ORGANIC LETTERS, 2002, 4 (15) :2549-2551
[8]   ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS [J].
CHATGILIALOGLU, C .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) :188-194
[9]   Differential carbohydrate recognition of two GlcNAc-6-sulfotransferases with possible roles in L-selectin ligand biosynthesis [J].
Cook, BN ;
Bhakta, S ;
Biegel, T ;
Bowman, KG ;
Armstrong, JI ;
Hemmerich, S ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (36) :8612-8622
[10]   THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].
CURRAN, DP .
SYNTHESIS-STUTTGART, 1988, (07) :489-513