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Volumn , Issue 7, 2008, Pages 1017-1020

Organocatalyzed asymmetric inverse-electron-demand hetero-Diels-Alder reaction of α,β-unsaturated trifluoromethyl ketones and aldehydes

Author keywords

Aldehyde; Dihydropyranone; Hetero Diels Alder reaction; Organocatalyzed; Unsaturated trifluoromethyl ketone

Indexed keywords

6 TRIFLUOROMETHYL 3,4 DIHYDROPYAN 2 ONES; DIPHENYLPROLINOL SILYL ETHER; ETHER DERIVATIVE; FLUORINE DERIVATIVE; TRIFLUOROMETHYLALDEHYDE; TRIFLUOROMETHYLKETONE;

EID: 42949123558     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042920     Document Type: Article
Times cited : (54)

References (48)
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    • For a general review of hetero-Diels-Alder reactions, see: a, Fringuelli, F, Taticchi, A, Eds, John Wiley and Sons: New York
    • For a general review of hetero-Diels-Alder reactions, see: (a) The Diels-Alder Reaction: Selected Practical Methods; Fringuelli, F.; Taticchi, A., Eds.; John Wiley and Sons: New York, 2002.
    • (2002) The Diels-Alder Reaction: Selected Practical Methods
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    • Kobayashi, S, Jørgensen, K. A, Eds, Wiley-VCH: Weinheim
    • (b) Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002, 151-209.
    • (2002) Cycloaddition Reactions in Organic Synthesis , pp. 151-209
  • 15
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    • Comprehensive Asymmetric Catalysis III; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 1237-1254.
    • (c) Comprehensive Asymmetric Catalysis III; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 1237-1254.
  • 21
    • 0022508443 scopus 로고    scopus 로고
    • The stoichiometric hetero-Diels-Alder reaction of chiral enamines with β,γ-unsaturated α-ketoesters has been reported earlier: (a) Eiden, F.; Winkler, W. Arch. Pharm. 1986, 319, 704.
    • The stoichiometric hetero-Diels-Alder reaction of chiral enamines with β,γ-unsaturated α-ketoesters has been reported earlier: (a) Eiden, F.; Winkler, W. Arch. Pharm. 1986, 319, 704.
  • 23
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    • For other examples of organocatalytic hetero-Diels-Alder reactions, see: c
    • For other examples of organocatalytic hetero-Diels-Alder reactions, see: (c) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 5962
    • Yamamoto, Y.1    Momiyama, N.2    Yamamoto, H.3
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    • 0022508443 scopus 로고    scopus 로고
    • For related stoichiometric examples, see: c
    • For related stoichiometric examples, see: (c) Eiden, F.; Winkler, W. Arch. Pharm. 1986, 319, 704.
    • (1986) Arch. Pharm , vol.319 , pp. 704
    • Eiden, F.1    Winkler, W.2
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    • For selected reviews on proline and its derivative-catalyzed reactions: a
    • For selected reviews on proline and its derivative-catalyzed reactions: (a) List, B. Acc. Chem. Res. 2004, 37, 548.
    • (2004) Acc. Chem. Res , vol.37 , pp. 548
    • List, B.1
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    • Notz, W.; Tanaka, F.; Barbas, C. F. III Acc. Chem. Res. 2004, 37, 580.
    • (b) Notz, W.; Tanaka, F.; Barbas, C. F. III Acc. Chem. Res. 2004, 37, 580.
  • 33
  • 39
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    • General Experimental Procedure To a stirred solution of aldehyde 1 (1.2 mmol, catalyst 11 (0.20 mmol, p-fluorophenol (0.20 mmol, and SiO2 (100 mg) in CH2Cl2 (10 ml) was added α,β-unsaturated trifluoromethyl ketones (1.0 mmol) at r.t. and the reaction mixture was stirred for the time as specified in Table 2 (monitored by TLC, The resulted mixture was directly purified by column chromatography on silica gel to give product 3. Jones reagent was added to the solution of 3 (0.8 mmol) in acetone (15 mL) at r.t. until the salmon pink of the solution did not disappear in one minute. The mixture was stirred at r.t. for 2 h and then quenched by MeOH (1 mL) and H2O (2 ml, The resulted mixture was extracted with Et2O (3 x 10 ml) and dried over Na2SO4. After removal of the solvent, the crude product of 7 was obtained and used in the next step directly without
    • R(major) = 26.4 min.
  • 40
    • 13444267885 scopus 로고    scopus 로고
    • For examples of (S)-diphenylpyrrolinol silyl ether promoted reactions, see: (a) Marigo, M, Wabnitz, T. C, Fielenbach, D, Jørgensen, K. A. Angew. Chem. Int. Ed. 2005, 44, 794
    • For examples of (S)-diphenylpyrrolinol silyl ether promoted reactions, see: (a) Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2005, 44, 794.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.