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Volumn 73, Issue 13, 2008, Pages 4903-4906

Asymmetric Syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINES; CHEMICAL REACTIONS; COPPER COMPOUNDS; LIGANDS; PYRIDINE;

EID: 46849105502     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800412x     Document Type: Article
Times cited : (118)

References (42)
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    • (a) Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1999; Vol. 2, pp 321-340.
    • (1999) Comprehensive Organic Synthesis , vol.2 , pp. 321-340
    • Rosini, G.1
  • 2
    • 0004148431 scopus 로고
    • Paquette, L. A, Ed, Wiley: New York, Chapter 3
    • (b) Pinnick, H. W. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1990; Vol. 38, Chapter 3.
    • (1990) Organic Reactions , vol.38
    • Pinnick, H.W.1
  • 3
    • 28644442668 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Berlin-Heidelberg, Germany, Chapter 29.3
    • (a) Shibasaki, M.; Gröger, H. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin-Heidelberg, Germany, 1999; Chapter 29.3.
    • (1999) Comprehensive Asymmetric Catalysis I-III
    • Shibasaki, M.1    Gröger, H.2
  • 8
    • 36849070344 scopus 로고    scopus 로고
    • And also see for a lanthanum-consisting catalyst: (c) Tur, F.; Saá, J. M. Org. Lett. 2007, 9, 5079-5082.
    • And also see for a lanthanum-consisting catalyst: (c) Tur, F.; Saá, J. M. Org. Lett. 2007, 9, 5079-5082.
  • 12
  • 18
    • 34250632623 scopus 로고    scopus 로고
    • (e) Ma, K.; You, J. Chem. Eur. J. 2007, 13, 1863-1871.
    • (2007) J. Chem. Eur. J , vol.13 , pp. 1863-1871
    • Ma, K.1    You2
  • 36
    • 0037725799 scopus 로고    scopus 로고
    • A study on Cu-catalyzed anti-selective Henry reaction: Risgaard, T.; Gothelf, K. V.; Jørgensen, K. A. Org. Biomol. Chem 2003, 1, 153-156.
    • A study on Cu-catalyzed anti-selective Henry reaction: Risgaard, T.; Gothelf, K. V.; Jørgensen, K. A. Org. Biomol. Chem 2003, 1, 153-156.
  • 37
    • 34548532744 scopus 로고    scopus 로고
    • Though we recently report a diastereoselective Henry reaction using newly developed diamine-Cu(OAc)2 catalyst, it was 80:20 syn/antiselectivity: Arai, T, Watanabe, M, Yanagisawa, A. Org. Lett. 2007, 9, 3595-3597
    • 2 catalyst, it was 80:20 syn/antiselectivity: Arai, T.; Watanabe, M.; Yanagisawa, A. Org. Lett. 2007, 9, 3595-3597.
  • 38
    • 0001040853 scopus 로고    scopus 로고
    • Representative reports on chiral sulfonyl-1,2-diamines in asymmetric catalysis: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562-7563.
    • Representative reports on chiral sulfonyl-1,2-diamines in asymmetric catalysis: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562-7563.
  • 41
    • 46849094186 scopus 로고    scopus 로고
    • 2i-CuCl-catalyzed diastereoselective Henry reaction of 3l with nitroethane gave the adduct in 58% yield with 82:18 synlanti selectivity. The enantiomeric excess of the syn-adduct was 60%.
    • 2i-CuCl-catalyzed diastereoselective Henry reaction of 3l with nitroethane gave the adduct in 58% yield with 82:18 synlanti selectivity. The enantiomeric excess of the syn-adduct was 60%.


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