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Volumn 45, Issue 29, 2006, Pages 4796-4798

Chiral Brønsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines

Author keywords

Asymmetric synthesis; Aza Diels Alder reaction; Br nsted acids; Enantioselectivity; Organocatalysis

Indexed keywords

ASYMMETRIC SYNTHESIS; AZA-DIELS-ALDER REACTION; BRØNSTED ACIDS; ENANTIOSELECTIVITY; ORGANOCATALYSIS;

EID: 33746801098     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601345     Document Type: Article
Times cited : (211)

References (78)
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    • For reviews on Brønsted acid catalysis, see: a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289;
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    • (Eds: A. Berkessel, H. Gröger), Wiley-VCH, Weinheim
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    • Wiley, New York, chap. 5
    • a value of diethyl phosphate is 1.39; see: L. D. Quin, A Guide to Organophosphorus Chemistry, Wiley, New York, 2000, chap. 5, pp. 133-165.
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    • see ref. [10b]
    • For organocatalyzed hetero-Diels-Alder reactions of aldehydes with Brassard's diene, see ref. [10b].
  • 74
    • 33746815933 scopus 로고    scopus 로고
    • CCDC-280243 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc. cam.ac.uk/data_request/cif.
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    • See Supporting Information for details
    • See Supporting Information for details.
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    • note
    • An aldimine derived from p-methoxyaniline exhibited lower enantioselectivity.
  • 77
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    • note
    • The nine-membered cyclic structure was observed as one of the energy minima of the complex derived from 2a and 4a by quantum chemical calculations (PM3, Spartan'02, Wavefunction, Inc.).
  • 78
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    • note
    • We suppose pyridine would not participate in the transition state but may stabilize Brassard's diene in the reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.