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Volumn 14, Issue 22, 2003, Pages 3613-3618

Halide ion effects in the rhodium-catalyzed allylic substitution reaction using copper(I) alkoxides and enolates

Author keywords

[No Author keywords available]

Indexed keywords

2 (BROMOMETHYL) 3 METHYL 4 (1 METHYLPROP 2 EN 1 YL) 5 PHENYL 2,3 DIHYDROFURAN; 3 METHYL 1 PHENYLPENT 4 EN 1 ONE; 3 METHYL 2 (1 METHYLPROP 2 EN 1 YL) 1 PHENYLPENT 4 EN 1 ONE; ALLYL COMPOUND; COPPER DERIVATIVE; ENOLASE; HALIDE; LITHIUM DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

EID: 0242541854     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.044     Document Type: Article
Times cited : (45)

References (41)
  • 1
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    • Wiley: New York; Chapter 4
    • For book chapters on metal-catalyzed allylic substitution, see: (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1996; Chapter 4, pp. 290-404; (b) Trost, B. M.; Lee, C. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8, pp. 593-649.
    • (1996) Palladium Reagents and Catalysts , pp. 290-404
    • Tsuji, J.1
  • 2
    • 0002177913 scopus 로고    scopus 로고
    • Ojima, I., Ed.; Wiley-VCH: New York; Chapter 8
    • For book chapters on metal-catalyzed allylic substitution, see: (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1996; Chapter 4, pp. 290-404; (b) Trost, B. M.; Lee, C. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8, pp. 593-649.
    • (2000) Catalytic Asymmetric Synthesis, 2nd Ed. , pp. 593-649
    • Trost, B.M.1    Lee, C.2
  • 29
    • 0001570202 scopus 로고
    • For an example of the transmetalation of a lithium enolate with a copper(I) halide salt, see:
    • For an example of the transmetalation of a lithium enolate with a copper(I) halide salt, see: Posner G.H., Lentz C.M. J. Am. Chem. Soc. 101:1979;934.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 934
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  • 32
    • 0038451395 scopus 로고    scopus 로고
    • For an example of the effect of alkali metal halides on regioselectivity in the allylic substitution with aryl zinc reagents, see:
    • For an example of the effect of alkali metal halides on regioselectivity in the allylic substitution with aryl zinc reagents, see: Evans P.A., Uraguchi D. J. Am. Chem. Soc. 125:2003;7158.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 7158
    • Evans, P.A.1    Uraguchi, D.2
  • 33
    • 0034829363 scopus 로고    scopus 로고
    • For an example of halide ligand and protic additives on enantioselectivity and reactivity in rhodium-catalyzed asymmetric ring-opening reactions, see: Lautens, M.; Fagnou, K, J. Am. Chem. Soc. 2001, 123, 7170. For a review on halide effects in transition metal-catalysis, see: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7170
    • Lautens, M.1    Fagnou, K.2
  • 34
    • 0037016413 scopus 로고    scopus 로고
    • For an example of halide ligand and protic additives on enantioselectivity and reactivity in rhodium-catalyzed asymmetric ring-opening reactions, see: Lautens, M.; Fagnou, K, J. Am. Chem. Soc. 2001, 123, 7170. For a review on halide effects in transition metal-catalysis, see: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 26
    • Fagnou, K.1    Lautens, M.2
  • 35
    • 37049133322 scopus 로고
    • Wilkinson's catalyst is known to undergo counter-ion exchange with lithium halides, see:
    • Wilkinson's catalyst is known to undergo counter-ion exchange with lithium halides, see: Osborn J.A., Jerdine F.H., Young J.F., Wilkinson G. J. Chem. Soc. (A). 1966;1711.
    • (1966) J. Chem. Soc. (A) , pp. 1711
    • Osborn, J.A.1    Jerdine, F.H.2    Young, J.F.3    Wilkinson, G.4
  • 36
    • 0000658620 scopus 로고
    • The trans-effect has been defined as: the effect of a coordinated group on the rate of substitution reactions of ligands trans to itself, see:
    • The trans-effect has been defined as: the effect of a coordinated group on the rate of substitution reactions of ligands trans to itself, see: Basolo F., Pearson R.G. Prog. Inorg. Chem. 4:1962;381.
    • (1962) Prog. Inorg. Chem. , vol.4 , pp. 381
    • Basolo, F.1    Pearson, R.G.2
  • 37
    • 0033800719 scopus 로고    scopus 로고
    • For a recent review on trans-effects in octahedral transition metal complexes, see:
    • For a recent review on trans-effects in octahedral transition metal complexes, see: Coe B.J., Glenwright S.J. Coord. Chem. Rev. 203:2000;5.
    • (2000) Coord. Chem. Rev. , vol.203 , pp. 5
    • Coe, B.J.1    Glenwright, S.J.2
  • 38
    • 85030935414 scopus 로고    scopus 로고
    • Previous studies demonstrated that α-substituted enolates are not prone to dialkylation under these reaction conditions
    • Previous studies demonstrated that α-substituted enolates are not prone to dialkylation under these reaction conditions.
  • 40
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    • For a related iodolactone desymmetrization, see:
    • For a related iodolactone desymmetrization, see: Kurth M.J., Brown E.G. J. Am. Chem. Soc. 109:1987;6844.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6844
    • Kurth, M.J.1    Brown, E.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.