Solid phase hydantoin synthesis: An efficient and direct conversion of Fmoc-protected dipeptides to hydantoins

被引:28
作者
Chong, PY [1 ]
Petillo, PA [1 ]
机构
[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
关键词
D O I
10.1016/S0040-4039(99)00243-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and direct conversion of Fmoc-protected dipeptides to hydantoins in the solid phase is described. This methodology uses MeSiCl3 in the presence of Et3N to cleave Fmoc-protected amines directly to their isocyanates. Internal cyclization of the amide on the isocyanate follows to produce the hydantoins in high purity and with no indication of racemization. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2493 / 2496
页数:4
相关论文
共 6 条
  • [1] Multilevel selectivity in the mild and high-yielding chlorosilane-induced cleavage of carbamates to isocyanates
    Chong, PY
    Janicki, SZ
    Petillo, PA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8515 - 8521
  • [2] DIVERSOMERS - AN APPROACH TO NONPEPTIDE, NONOLIGOMERIC CHEMICAL DIVERSITY
    DEWITT, SH
    KIELY, JS
    STANKOVIC, CJ
    SCHROEDER, MC
    CODY, DMR
    PAVIA, MR
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (15) : 6909 - 6913
  • [3] Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization cleavage step
    Dressman, BA
    Spangle, LA
    Kaldor, SW
    [J]. TETRAHEDRON LETTERS, 1996, 37 (07) : 937 - 940
  • [4] Solid-phase organic reactions: A review of the recent literature
    Hermkens, PHH
    Ottenheijm, HCJ
    Rees, D
    [J]. TETRAHEDRON, 1996, 52 (13) : 4527 - 4554
  • [5] Efficient solid phase synthesis of 3,5-disubstituted hydantoins
    Nefzi, A
    Ostresh, JM
    Giulianotti, M
    Houghten, RA
    [J]. TETRAHEDRON LETTERS, 1998, 39 (45) : 8199 - 8202
  • [6] Xiao XY, 1997, J ORG CHEM, V62, P6968