Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-substituted pyrrole derivatives

被引:21
作者
Demir, AS [1 ]
Akhmedov, IM [1 ]
Sesenoglu, Ö [1 ]
Alptürk, O [1 ]
Apaydin, S [1 ]
Gerçek, Z [1 ]
Ibrahimzade, N [1 ]
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 10期
关键词
Alcohols - Amines - Amino acids - Derivatives - Esters - Synthesis (chemical);
D O I
10.1039/b008317h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The conversion of the amino group of chiral amines, amino alcohols, amino acids and their esters into chiral 2-substituted pyrrole derivatives with various halogeno enones is described. The conversion works in good yield and without racemization. The synthesis of 2-phenylpyrrole derivatives was possible with amino alcohols but not with amino acids or their esters.
引用
收藏
页码:1162 / 1167
页数:6
相关论文
共 34 条
  • [1] Synthesis and antitumor activity of duocarmycin derivatives:: A-ring pyrrole compounds bearing (β-(5′,6′,7′-trimethoxy-2′-indolyl)acryloyl group
    Amishiro, N
    Nagamura, S
    Kobayashi, E
    Okamoto, A
    Gomi, K
    Okabe, M
    Saito, H
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (07) : 1637 - 1643
  • [2] RECENT ADVANCES IN CHEMISTRY OF PYRROLE
    BALTAZZI, E
    [J]. CHEMICAL REVIEWS, 1963, 63 (05) : 511 - +
  • [3] ACYLATION OF UNSATURATED HALIDES, ALCOHOLS, ESTERS AND KETONES
    BARBRY, D
    FAVEN, C
    AJANA, A
    [J]. SYNTHETIC COMMUNICATIONS, 1993, 23 (19) : 2647 - 2658
  • [4] BARTON DHR, 1990, TETRAHEDRON, V46, P7587
  • [5] Bird C.W., 1984, COMPREHENSIVE HETERO, V4
  • [6] Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents
    Caldarelli, M
    Habermann, J
    Ley, SV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02): : 107 - 110
  • [7] COQUERET X, 1983, TETRAHEDRON LETT, V34, P5382
  • [8] A new approach to porphobilinogen and its analogs
    deLeon, CY
    Ganem, B
    [J]. TETRAHEDRON, 1997, 53 (23) : 7731 - 7752
  • [9] Conversion of homochiral amines, beta-amino alcohols and alpha-amino acids to their chiral 2-methylpyrrole derivatives
    Demir, AS
    Akhmedov, IM
    Tanyeli, C
    Gercek, Z
    Gadzhili, RA
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (05) : 753 - 757
  • [10] A facile synthesis of polysubstituted pyrroles
    Dieter, RK
    Yu, HY
    [J]. ORGANIC LETTERS, 2000, 2 (15) : 2283 - 2286