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Volumn 130, Issue 48, 2008, Pages 16162-16163

Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: Asymmetric synthesis of allyl oxindoles

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; HALIDE; LEWIS ACID; OXINDOLE; PALLADIUM; PERCHLORATE; TRIFLUOROMETHANESULFONIC ACID;

EID: 57149110232     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807026z     Document Type: Article
Times cited : (157)

References (34)
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    • Castro, A.M.M.1
  • 4
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    • For reviews of asymmetric Claisen rearrangements:(a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43-50.
    • For reviews of asymmetric Claisen rearrangements:(a) Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43-50.
  • 7
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    • Hiersemann, M, Nubbemeyer, U, Eds, Wiley-VCH: Weinheim, Germany
    • Hiersemann, M., Nubbemeyer, U., Eds. The Claisen Rearrangment; Wiley-VCH: Weinheim, Germany, 2007.
    • (2007) The Claisen Rearrangment
  • 13
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    • For a classic example where turnover is problematic, see
    • For a classic example where turnover is problematic, see: Yamamoto, H.; Maruoka, K. Pure Appl. Chem. 1990, 62, 2063-2068.
    • (1990) Pure Appl. Chem , vol.62 , pp. 2063-2068
    • Yamamoto, H.1    Maruoka, K.2
  • 14
    • 84889308411 scopus 로고    scopus 로고
    • The Meerwein-Eschenmoser-Claisen Rearrangement
    • Hiersemann, M, Nubbemeyer, U, Eds, Wiley-VCH: Weinheim
    • Gradl, S. N.; Trauner, D. The Meerwein-Eschenmoser-Claisen Rearrangement. In The Claisen Rearrangement; Hiersemann, M., Nubbemeyer, U., Eds.; Wiley-VCH: Weinheim, 2007; pp 367-396.
    • (2007) The Claisen Rearrangement , pp. 367-396
    • Gradl, S.N.1    Trauner, D.2
  • 16
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    • Selected natural products:(a) Takano, S.; Ogasawara, K. Alkaloids 1989, 36, 225-251.
    • Selected natural products:(a) Takano, S.; Ogasawara, K. Alkaloids 1989, 36, 225-251.
  • 20
    • 22944473048 scopus 로고    scopus 로고
    • Selected biological agents: (a) Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qiu, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Tomita, Y.; Parrish, D. A.; Deschamps, J. R.; Wang, S. J. Am. Chem. Soc. 2005, 127, 10130-10131.
    • Selected biological agents: (a) Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qiu, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Tomita, Y.; Parrish, D. A.; Deschamps, J. R.; Wang, S. J. Am. Chem. Soc. 2005, 127, 10130-10131.
  • 29
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    • There is also a report of trimethylenemethane [3 + 2]-cycloaddition to yield chiral oxindoles containing spiro ring systems at C3: Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396-12397.
    • There is also a report of trimethylenemethane [3 + 2]-cycloaddition to yield chiral oxindoles containing spiro ring systems at C3: Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396-12397.
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    • See Supporting Information
    • See Supporting Information.
  • 32
    • 57149094960 scopus 로고    scopus 로고
    • Surprisingly, lowering the temperature to improve enantioselectivity caused a disproportionate change in the rate (>12 h at-20°C).
    • Surprisingly, lowering the temperature to improve enantioselectivity caused a disproportionate change in the rate (>12 h at-20°C).
  • 34
    • 34247531301 scopus 로고    scopus 로고
    • Alternately, rearrangement via double bond activation may be possible: Watson, M. P.; Overman, L. E.; Bergman, R. G. J. Am. Chem. Soc. 2007, 129, 5031-5044.
    • Alternately, rearrangement via double bond activation may be possible: Watson, M. P.; Overman, L. E.; Bergman, R. G. J. Am. Chem. Soc. 2007, 129, 5031-5044.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.