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Volumn 53, Issue 11, 2014, Pages 2997-3000

Asymmetric vinylogous diels-alder reactions catalyzed by a chiral phosphoric acid

Author keywords

asymmetric catalysis; Br nsted acids; Diels Alder reactions; organocatalysis; synthetic methods

Indexed keywords

ASYMMETRIC CATALYSIS; DIELS-ALDER REACTION; ORGANOCATALYSIS; REMOTE STEREOCONTROL; SYNTHETIC METHODS; SYNTHETIC UTILITY; TETRAHYDROCARBAZOLES; VINYLOGOUS REACTIVITIES;

EID: 84896752366     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201310487     Document Type: Article
Times cited : (96)

References (53)
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    • 2+ ions in combination with phosphoric acid catalysts has been reported; see
    • 2+ ions in combination with phosphoric acid catalysts has been reported; see:, M. Hatano, K. Moriyama, T. Maki, K. Ishihara, Angew. Chem. 2010, 122, 3911
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    • We performed a control experiment using a sample of commercially available catalyst 4 d that had been further purified by a careful extraction with HCl. This experiment provided a similar reactivity and stereoselectivity (3 a obtained in 88 % yield, 88 % ee), indicating that metals are not involved in the reported reaction.
    • Angew. Chem. Int. Ed. 2010, 49, 3823. We performed a control experiment using a sample of commercially available catalyst 4 d that had been further purified by a careful extraction with HCl. This experiment provided a similar reactivity and stereoselectivity (3 a obtained in 88 % yield, 88 % ee), indicating that metals are not involved in the reported reaction.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 3823
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    • 84896799997 scopus 로고    scopus 로고
    • CCDC 973586 contains the supplementary crystallographic data for this paper (3 e). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 973586 contains the supplementary crystallographic data for this paper (3 e). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 47
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    • This pathway can be catalyzed by a strong Brønsted acid as previously reported; see.
    • This pathway can be catalyzed by a strong Brønsted acid as previously reported; see:, C. B. Chen, X. F. Wang, Y. J. Cao, H. G. Cheng, W.-J. Xiao, J. Org. Chem. 2009, 74, 3532.
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    • for a recent report on a negative NLE associated with chiral phosphoric acid catalysis, see
    • Angew. Chem. Int. Ed. 2009, 48, 456; for a recent report on a negative NLE associated with chiral phosphoric acid catalysis, see
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 456
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    • 0=0.025 M, stirring at 40 °C for 16 h). A positive NLE was also observed when performing the experiments in chloroform. For a pertinent discussion, see
    • 0=0.025 M, stirring at 40 °C for 16 h). A positive NLE was also observed when performing the experiments in chloroform. For a pertinent discussion, see:, N. Li, X.-H. Chen, S.-M. Zhou, S.-W. Luo, J. Song, L. Ren, L.-Z. Gong, Angew. Chem. 2010, 122, 6522
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    • Li, N.1    Chen, X.-H.2    Zhou, S.-M.3    Luo, S.-W.4    Song, J.5    Ren, L.6    Gong, L.-Z.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.