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Volumn 34, Issue 6, 1995, Pages 676-678

Carbenoid Transfer to Imines: A New Asymmetric Catalytic Synthesis of Aziridines

Author keywords

asymmetric synthesis; aziridines; chiral ligands; copper complexes

Indexed keywords


EID: 33748236032     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199506761     Document Type: Article
Times cited : (243)

References (41)
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    • For a discussion on the development and application of chiral bis(dihydrooxazole)s and related ligands in asymmetric catalysis, see
    • (1993) Acc. Chem. Res. , vol.26 , pp. 339-345
    • Pfaltz, A.1
  • 22
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    • N‐Aryl aziridines undergo rapid inversion at nitrogen, and thus the configuration at nitrogen is not an issue in the present case. (a)
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 352-356
    • Anet, F.A.1    Osyany, J.M.2
  • 24
    • 84985621200 scopus 로고    scopus 로고
    • 3] and ( R)‐2,2,2‐trifluoro‐1‐(9‐anthryl)‐ethanol [10]. The peaks of the enantiomers were assigned by comparison to racemic material (prepared by employing racemic 4a).
  • 26
    • 84985546383 scopus 로고
    • Ligand 4d was prepared from dimethyl malononitrile and ethanolamine according to, Liebigs Ann. Chem., 996–1009.
    • (1974)
    • Witte, H.1    Seeliger, W.2
  • 27
    • 84985549298 scopus 로고    scopus 로고
    • Other substrates screened include alkylimines, tosylimines, O‐methyloximes, and N,N‐dimethylhydrazones.
  • 28
    • 84985555903 scopus 로고    scopus 로고
    • The formation of fumarate and maleate by‐products in copper‐catalyzed reactions of diazoesters is a well‐known and practically inevitable reaction [5f].
  • 33
    • 0038094260 scopus 로고
    • Generation and utilization of carbonyl ylides via the tandem cyclization-cycloaddition method
    • (a) For a review of the chemistry of ylides formed from the reaction of heteroatom nucleophiles with carbenes, see
    • (1991) Accounts of Chemical Research , vol.24 , pp. 22-28
    • Padwa, A.1
  • 35
    • 84985515548 scopus 로고    scopus 로고
    • In this context, we have observed that while N‐benzylidenebenzylamine is not an effective substrate for aziridination, it does react under the prescribed conditions to produce trace quantities of the adduct arising from dipolar cycloaddition of the corresponding azomethine ylide.
  • 37
    • 0000146695 scopus 로고
    • Chirale Phosphinoaryldihydrooxazole als Liganden in der asymmetrischen Katalyse: Pd-katalysierte allylische Substitution
    • (1993) Angewandte Chemie , vol.105 , pp. 614-616
    • Von Matt, P.1    Pfaltz, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.