DIBAL-H-H2NR and DIBAL-H-HNR1R2•HCl complexes for efficient conversion of lactones and esters to amides

被引:59
作者
Huang, PQ [1 ]
Zheng, X [1 ]
Deng, XM [1 ]
机构
[1] Xiamen Univ, Dept Chem, Xiamen 361005, Peoples R China
基金
中国国家自然科学基金;
关键词
aminolysis; DIBAL H; Weinreb amides; amides;
D O I
10.1016/S0040-4039(01)01933-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of a lactone or an ester with organoaluminum species generated from DIBAL-H-H2NR or DIBAL-H-(HNRR2)-R-1-HCl complexes provided efficient methods for preparation of amides. Conditions were defined for the preparation of both secondary and tertiary amides, including Weinreb amides in excellent yields, (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9039 / 9041
页数:3
相关论文
共 18 条
  • [1] BASHA A, 1977, TETRAHEDRON LETT, P4171
  • [2] BARRELENE DERIVATIVES - POTENTIAL MODULES FOR ASSEMBLY
    BEERLI, R
    REBEK, J
    [J]. TETRAHEDRON LETTERS, 1995, 36 (11) : 1813 - 1816
  • [3] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN
    EVANS, DA
    KALDOR, SW
    JONES, TK
    CLARDY, J
    STOUT, TJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) : 7001 - 7031
  • [4] TOTAL SYNTHESIS OF (+)-ACTINOBOLIN
    GARIGIPATI, RS
    TSCHAEN, DM
    WEINREB, SM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) : 7790 - 7792
  • [5] Preparation of optically active α,α-difluoro-β-hydroxyketones
    Iseki, K
    Asada, D
    Kuroki, Y
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1999, 97 (1-2) : 85 - 89
  • [6] Lee JI, 2001, B KOR CHEM SOC, V22, P421
  • [7] AN ALTERNATIVE PROCEDURE FOR THE ALUMINUM-MEDIATED CONVERSION OF ESTERS TO AMIDES
    LEVIN, JI
    TUROS, E
    WEINREB, SM
    [J]. SYNTHETIC COMMUNICATIONS, 1982, 12 (13) : 989 - 993
  • [8] Lipton M. F., 1979, Org. Synth., V59, P49, DOI DOI 10.15227/ORGSYN.059.0049
  • [9] A mild method for ring-opening aminolysis of lactones
    Liu, WM
    Xu, DD
    Repic, O
    Blacklock, TJ
    [J]. TETRAHEDRON LETTERS, 2001, 42 (13) : 2439 - 2441
  • [10] Total synthesis of lembehyne A, a neuritogenic spongean polyacetylene
    Murakami, N
    Nakajima, T
    Kobayashi, M
    [J]. TETRAHEDRON LETTERS, 2001, 42 (10) : 1941 - 1943