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
    ADLINGTON, RM
    BALDWIN, JE
    BASAK, A
    KOZYROD, RP
    [J]. 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
    ATHERTON, E
    SHEPPARD, RC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (03) : 165 - 166
  • [5] Formation of monomeric halogenoaryl acrylates in the presence of hindered pyridine bases
    Blazejewski, JC
    Hofstraat, JW
    Lequesne, C
    Wakselman, C
    Wiersum, UE
    [J]. 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
    Caddick, S
    Hamza, D
    Wadman, SN
    Wilden, JD
    [J]. ORGANIC LETTERS, 2002, 4 (10) : 1775 - 1777
  • [7] A new route to sulfonamides via intermolecular radical addition to pentafluorophenyl vinylsulfonate and subsequent aminolysis
    Caddick, S
    Wilden, JD
    Bush, HD
    Wadman, SN
    Judd, DB
    [J]. ORGANIC LETTERS, 2002, 4 (15) : 2549 - 2551
  • [8] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS
    CHATGILIALOGLU, C
    [J]. 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
    Cook, BN
    Bhakta, S
    Biegel, T
    Bowman, KG
    Armstrong, JI
    Hemmerich, S
    Bertozzi, CR
    [J]. 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.
    CURRAN, DP
    [J]. SYNTHESIS-STUTTGART, 1988, (07): : 489 - 513