Highly stereoselective allylic alkylations of peptides

被引:52
作者
Kazmaier, Uli [1 ]
Deska, Jan [1 ]
Watzke, Anja [1 ]
机构
[1] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany
关键词
allylation; asymmetric synthesis; chelates; palladium; peptides;
D O I
10.1002/anie.200600509
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Help from the neighbors: Palladium-catalyzed allylic alkylations are extremely suitable for the stereoselective introduction of unsaturated side chains to peptides (see scheme; TFA = trifluoroacetate). The chiral information of the peptide can be used to control the formation of the new stereogenic center. In general, S amino acids induce the formation of R-configured amino acids. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4855 / 4858
页数:4
相关论文
共 43 条
  • [1] [Anonymous], MODERN SYNTHETIC MET
  • [2] [Anonymous], 1992, ALDRICHIM ACTA
  • [3] CONVERSION OF SERINE AND THREONINE RESIDUES INTO ALPHA-ACYLOXY-HALOGENOGLYCINE, ALPHA-ALKYLTHIO-HALOGENOGLYCINE, AND ALPHA-HALOGENOGLYCINE MOIETIES - A NEW STRATEGY FOR THE MODIFICATION OF PEPTIDES
    APITZ, G
    STEGLICH, W
    [J]. TETRAHEDRON LETTERS, 1991, 32 (27) : 3163 - 3166
  • [4] Iodination of aromatic residues in peptides by reaction with IPy(2)BF(4)
    Barluenga, J
    GarciaMartin, MA
    Gonzalez, JM
    Clapes, P
    Valencia, G
    [J]. CHEMICAL COMMUNICATIONS, 1996, (13) : 1505 - 1506
  • [5] A NEW APPROACH TO THE SYNTHESIS OF DIPEPTIDES WITH UNNATURAL AMINO-ACIDS USING ORGANOZINC CHEMISTRY
    DUNN, MJ
    GOMEZ, S
    JACKSON, RFW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13): : 1639 - 1640
  • [6] SELECTIVE MODIFICATION OF GLYCINE RESIDUES IN DIPEPTIDES
    EASTON, CJ
    SCHARFBILLIG, IM
    TAN, EW
    [J]. TETRAHEDRON LETTERS, 1988, 29 (13) : 1565 - 1568
  • [7] Free-radical reactions in the synthesis of alpha-amino acids and derivatives
    Easton, CJ
    [J]. CHEMICAL REVIEWS, 1997, 97 (01) : 53 - 82
  • [8] FLIRI H, 1993, ANTIBIOTICS ANTIVIRA, P229
  • [9] BIOACTIVE SPONGE PEPTIDES
    FUSETANI, N
    MATSUNAGA, S
    [J]. CHEMICAL REVIEWS, 1993, 93 (05) : 1793 - 1806
  • [10] ENHANCEMENT OF DETECTION SENSITIVITY OF CYCLOSPORIN A BY DERIVATIZATION WITH 2-NAPHTHYLSELENYLCHLORIDE
    GFELLER, JC
    BECK, AK
    SEEBACH, D
    [J]. HELVETICA CHIMICA ACTA, 1980, 63 (03) : 728 - 732