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
  • [31] C-ALKYLATION OF SARCOSINE RESIDUES IN CYCLIC TETRAPEPTIDES VIA LITHIUM ENOLATES
    MILLER, SA
    GRIFFITHS, SL
    SEEBACH, D
    [J]. HELVETICA CHIMICA ACTA, 1993, 76 (01) : 563 - 595
  • [32] Selective side chain introduction onto small peptides mediated by samarium diiodide:: A potential route to peptide libraries
    Ricci, M
    Blakskjær, P
    Skrydstrup, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (50) : 12413 - 12421
  • [33] Ricci M, 2000, ANGEW CHEM INT EDIT, V39, P242, DOI 10.1002/(SICI)1521-3773(20000103)39:1<242::AID-ANIE242>3.0.CO
  • [34] 2-R
  • [35] RICCI M, 2000, ANGEW CHEM, V112, P248
  • [36] MODIFICATION OF CYCLOSPORINE-A (CS) - GENERATION OF AN ENOLATE AT THE SARCOSINE RESIDUE AND REACTIONS WITH ELECTROPHILES
    SEEBACH, D
    BECK, AK
    BOSSLER, HG
    GERBER, C
    KO, SY
    MURTIASHAW, CW
    NAEF, R
    SHODA, S
    THALER, A
    KRIEGER, M
    WENGER, R
    [J]. HELVETICA CHIMICA ACTA, 1993, 76 (04) : 1564 - 1590
  • [37] STRUCTURE AND REACTIVITY OF LITHIUM ENOLATES - FROM PINACOLONE TO SELECTIVE C-ALKYLATIONS OF PEPTIDES - DIFFICULTIES AND OPPORTUNITIES AFFORDED BY COMPLEX STRUCTURES
    SEEBACH, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (12): : 1624 - 1654
  • [38] Seebach D, 1988, ANGEW CHEM, V100, P1685
  • [39] Severin K, 1998, ANGEW CHEM INT EDIT, V37, P126, DOI 10.1002/(SICI)1521-3773(19980202)37:1/2<126::AID-ANIE126>3.0.CO
  • [40] 2-4