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Volumn 126, Issue 2, 2004, Pages 456-457

Chiral Copper Complexes of Phosphino Sulfenyl Ferrocenes as Efficient Catalysts for Enantioselective Formal Aza Diels-Alder Reactions of N-Sulfonyl Imines

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; FERROCENE DERIVATIVE; IMINE; N SULFONYLIMINE DERIVATIVE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0347717646     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038494y     Document Type: Article
Times cited : (181)

References (23)
  • 4
    • 0003900659 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: San Diego
    • (d) Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2001: Vol. 55.
    • (2001) The Alkaloids , vol.55
    • Michael, J.P.1
  • 6
    • 0000862669 scopus 로고    scopus 로고
    • For a review on catalytic enantioselective additions to imines, see: Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
    • (1999) Chem. Rev. , vol.99 , pp. 1069
    • Kobayashi, S.1    Ishitani, H.2
  • 7
    • 0001294788 scopus 로고
    • This transformation was first achieved by Yamamoto using a stoichiometric amount of a chiral boron complex: Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264.
    • (1992) J. Org. Chem. , vol.57 , pp. 3264
    • Hattori, K.1    Yamamoto, H.2
  • 17
    • 0346465004 scopus 로고    scopus 로고
    • note
    • See Supporting Information for detailed X-ray data.
  • 18
    • 0347725837 scopus 로고    scopus 로고
    • note
    • 2, rt), giving rise to the dihydropyridine 5a in 55% ee from (R)-1a and 73% ee from (R)-1f (67-68% chemical yield).
  • 21
    • 0346465002 scopus 로고    scopus 로고
    • John Wiley & Sons: New York
    • For instance, the tosylamides 5a and 5g, having an aryl and an alkenyl group at C-2 respectively, afforded the chiral 4-oxopiperidines 8a and 8g in satisfactory yields (58-64%, unoptimized) upon treatment with Zn/ AcOH at room temperature. For the deprotection of sulfonamides, see: (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed; John Wiley & Sons: New York, 1999; p 603-615. For the selective deprotection of p-nitrophenyl sulfonamides, see:
    • (1999) Protective Groups in Organic Synthesis, 3rd Ed , pp. 603-615
    • Greene, T.W.1    Wuts, P.G.M.2
  • 23
    • 0347725836 scopus 로고    scopus 로고
    • note
    • 2 provided enantiomerically pure compounds (>99.5% ee, 60-70% yield).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.