Multicomponent reactions .2. Stereoselective synthesis of 1(S)-camphor-2-cis-methylidene-isocyanide and its application in Passerini- and Ugi-reaction

被引：42
作者：
Bock, H [1 ]
Ugi, I [1 ]
机构：
[1] TECH UNIV MUNICH,INST ORGAN CHEM & BIOCHEM,D-85747 GARCHING,GERMANY
来源：
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1997年 / 339卷 / 04期
关键词：
D O I：
10.1002/prac.19973390167
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The use of unsaturated isocyanides in multicomponent reactions leads to N-vinylamides, which can be cleaved to carboxylic acids or esters under mild conditions. The chiral 1 (S)-camphor-2-cis-methylidene-isocyanide (5) can be prepared in two steps from camphor and methylisocyanide. Its application in the Passerini reaction generates alpha-acyloxyamides (6, 7, 8, 9) with a diastereomeric excess of > 92%, in the Ugi reaction alpha-acylaminoamides with a diastereomeric excess of 0% are formed.
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页码：385 / 389
页数：5
相关论文
共 19 条
  • [1] RECOVERY OF CHIRAL ALPHA-FERROCENYLALKYLAMINES ON STEREOSELECTIVE PEPTIDE-SYNTHESIS BY 4-COMPONENT CONDENSATION
    EBERLE, G
    UGI, I
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (08): : 492 - 493
  • [2] EBERLE G, 1976, ANGEW CHEM, V88, P509
  • [3] FELDER ER, 1994, CHIMIA, V48, P531
  • [4] GENERAL-METHOD FOR RAPID SYNTHESIS OF MULTICOMPONENT PEPTIDE MIXTURES
    FURKA, A
    SEBESTYEN, F
    ASGEDOM, M
    DIBO, G
    [J]. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1991, 37 (06): : 487 - 493
  • [5] ALPHA-METALATED ISOCYANIDES IN ORGANIC SYNTHESIS
    HOPPE, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (12) : 789 - 804
  • [6] HOPPE D, 1974, ANGEW CHEM, V86, P878
  • [7] MOLECULAR DIVERSITY VIA A CONVERTIBLE ISOCYANIDE IN THE UGI 4-COMPONENT CONDENSATION
    KEATING, TA
    ARMSTRONG, RW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (29) : 7842 - 7843
  • [8] STEREOSELECTIVE SYNTHESES OF PEPTIDE DERIVATIVES WITH 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-1-AMINO-2-DEOXY-BETA-D-GLUCOPYRANOSE BY 4-COMPONENT CONDENSATION
    LEHNHOFF, S
    GOEBEL, M
    KARL, RM
    KLOSEL, R
    UGI, I
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10): : 1104 - 1107
  • [9] Lehnhoff S., 1995, ANGEW CHEM, V107, P1208
  • [10] Ltidke G., 1971, ISONITRILE CHEM, P145, DOI DOI 10.1039/C3CC47156J
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