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Volumn 69, Issue 4, 2004, Pages 1309-1320

Controllable Enantioselective Friedel-Crafts Reaction between Indoles and Alkylidene Malonates Catalyzed by Pseudo-C3-Symmetric Trisoxazoline Copper(II) Complexes

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; ALKYLATION; CATALYSTS; COMPLEXATION; ETHANE; ORGANIC SOLVENTS; STEREOCHEMISTRY;

EID: 1242352444     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035552p     Document Type: Article
Times cited : (179)

References (166)
  • 1
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    • This reaction can also be viewed as a Michael addition reaction, but the majority of literatures regarded such a reaction as a Friedel-Crafts reaction, please see refs 11b, 11c, 20 and: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4370
    • Paras, N.A.1    MacMillan, D.W.C.2
  • 30
    • 0001320447 scopus 로고    scopus 로고
    • For cycloadditions of silyl ketenes, see: (l) Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125.
    • (2001) Org. Lett. , vol.3 , pp. 2125
    • Evans, D.A.1    Janey, J.M.2
  • 92
    • 0033714636 scopus 로고    scopus 로고
    • For introducing additional donating atoms to the chiral ligand to stabilize the active intermediates, see: (a) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
    • (2000) Chem. Rev. , vol.100 , pp. 2159
    • Fache, F.1    Schulz, E.2    Tommasino, M.L.3    Lemaire, M.4
  • 103
    • 0035926420 scopus 로고    scopus 로고
    • Alkylidene malonates were widely used in the Michael addition, see, for example: (a) Alexakis, A.; Benhaim, C. Tetrahedron: Asymmetry 2001, 12, 1151.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1151
    • Alexakis, A.1    Benhaim, C.2
  • 126
    • 0027943133 scopus 로고
    • For representative examples of catalytic processes that utilize alcohols as additives see: (a) Kawara, A.; Taguchi, T. Tetrahedron Lett. 1994, 35, 8805.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8805
    • Kawara, A.1    Taguchi, T.2
  • 136
    • 0001045470 scopus 로고
    • For the reversal of stereochemistry by additives in catalysis, please see: (a) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4083
    • Kobayashi, S.1    Ishitani, H.2
  • 145
    • 0037037983 scopus 로고    scopus 로고
    • For the reversal of stereochemistry by temperature in catalysis, please see: (a) Sibi, M. P.; Gorikunti, U.; Liu, M. Tetrahedron 2002, 58, 8357.
    • (2002) Tetrahedron , vol.58 , pp. 8357
    • Sibi, M.P.1    Gorikunti, U.2    Liu, M.3
  • 147
    • 0029872590 scopus 로고    scopus 로고
    • For the reversal of stereochemistry by solvents in catalysis, please see: (a) Johannsen, M.; Jørgensen, K. A. Tetrahedron 1996, 52, 7321.
    • (1996) Tetrahedron , vol.52 , pp. 7321
    • Johannsen, M.1    Jørgensen, K.A.2
  • 154
  • 160
    • 1242291313 scopus 로고    scopus 로고
    • note
    • It should be noted that product with 90% ee was added to isobutyl alcohol solution while product with 77% ee was added to acetone solution, since reaction afforded product with 90% ee in isobutyl alcohol but 77% ee in acetone at 15 °C.
  • 162
    • 0037424062 scopus 로고    scopus 로고
    • Both bisoxazoline 1c/KOTf and trisoxazoline 2a/KOTf were unable to catalyze this reaction. In a recent report, KOTf was found to catalyze aza Diels-Alder reactions of Danishefsky's diene with imines in water smoothly, please see: Loncaric, C.; Manabe, K.; Kobayashi, S. Chem. Commun. 2003, 574.
    • (2003) Chem. Commun. , pp. 574
    • Loncaric, C.1    Manabe, K.2    Kobayashi, S.3
  • 165
    • 1242336274 scopus 로고    scopus 로고
    • note
    • 3 vibrational modes are not discussed.
  • 166
    • 1242268731 scopus 로고    scopus 로고
    • note
    • For more information, please see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.