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Volumn 2, Issue 4, 1996, Pages 462-469

A novel route to racemic and nonracemic products of the Ugi reaction: Synthesis of Ugi's labile α-adducts from iminoaziridines and carboxylic acids, and their transformations

Author keywords

Aziridines; Imides; Isoimides; Rearrangements; Ugi reaction

Indexed keywords

AZIRIDINES; IMIDES; ISOIMIDES; REARRANGEMENTS; UGI REACTION;

EID: 0010425467     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020417     Document Type: Article
Times cited : (22)

References (81)
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    • The results are taken from the dissertation of S. Aldenkortt, University of Würzburg, 1995
    • The results are taken from the dissertation of S. Aldenkortt, University of Würzburg, 1995.
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    • For the work of others in this field, see for example
    • For the work of others in this field, see for example: M. Waki, J. Meienhofer, J. Am. Chem. Soc. 1977, 99, 6075-6082;
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 6075-6082
    • Waki, M.1    Meienhofer, J.2
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    • Diploma Thesis, University of Würzburg
    • B. Freudenreich, Diploma Thesis, University of Würzburg, 1972.
    • (1972)
    • Freudenreich, B.1
  • 47
    • 84891288014 scopus 로고    scopus 로고
    • For the use of 2,2-dimethylpropanal in the Ugi reaction see ref. [15]
    • For the use of 2,2-dimethylpropanal in the Ugi reaction see ref. [15].
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    • (Ed.: J. D. Morrison). Academic Press, New York
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    • All hitherto isolated acyclic isoimides (O-acyl isoamides, O-acyl imidates, imino anhydrides) adopt the (Z) configuration of the C=N group and are stabilised by special groups (-NRAr, -OR) at the nitrogen atom that retard the (Z) → (E) diastereomerisation, which is the rate-limiting step of the Mumm rearrangement in these cases
    • All hitherto isolated acyclic isoimides (O-acyl isoamides, O-acyl imidates, imino anhydrides) adopt the (Z) configuration of the C=N group and are stabilised by special groups (-NRAr, -OR) at the nitrogen atom that retard the (Z) → (E) diastereomerisation, which is the rate-limiting step of the Mumm rearrangement in these cases: I. Hagedorn, Angew. Chem. 1963, 75, 304;
    • (1963) Angew. Chem. , vol.75 , pp. 304
    • Hagedorn, I.1
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    • J. Am. Chem. Soc. 1967, 89, 637-645;
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    • Formation and rate of the Mumm rearrangement of N-aryl-O-benzoyl isobenzamides studied by IR spectroscopy
    • a) Formation and rate of the Mumm rearrangement of N-aryl-O-benzoyl isobenzamides studied by IR spectroscopy: J. S. P. Schwarz, J. Org. Chem. 1972, 37, 2906-2908;
    • (1972) J. Org. Chem. , vol.37 , pp. 2906-2908
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  • 61
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    • Rate of the Mumm rearrangement of O-acyl-N-aryl isobenzamides studied by UV spectroscopy
    • b) Rate of the Mumm rearrangement of O-acyl-N-aryl isobenzamides studied by UV spectroscopy: K. Brady, A. F. Hegarty, J. Chem. Soc. Perkin Trans. 2 1980, 121-126.
    • (1980) J. Chem. Soc. Perkin Trans. 2 , pp. 121-126
    • Brady, K.1    Hegarty, A.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.