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Volumn 72, Issue 24, 2007, Pages 9253-9258

Synthesis of chiral 3-substituted indanones via an enantioselective reductive-heck reaction

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; ENANTIOSELECTIVITY; REDUCTION; SYNTHESIS (CHEMICAL);

EID: 36649010182     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701741y     Document Type: Article
Times cited : (136)

References (55)
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    • Preparation of indanes as modulaters of glucocorticoid receptor, AP-1, or NF-κ B activity for use as antiobesity, antidiabetic, anti-inflammatory, or immunomodulatory agents
    • WO 2007073503 A2, June 28, 2007
    • (a) Bristol-Myers Squibb Company; Preparation of indanes as modulaters of glucocorticoid receptor, AP-1, or NF-κ B activity for use as antiobesity, antidiabetic, anti-inflammatory, or immunomodulatory agents. WO 2007073503 A2, June 28, 2007.
  • 20
    • 36649024266 scopus 로고    scopus 로고
    • For Rhodium-catalyzed asymmetric synthesis of 3,3-disubstituted 1-indanones, see: Shintani, R.; Takatsu, K.; Hayashi, T. Angew. Chem. 2007, 119, 3809;
    • (b) For Rhodium-catalyzed asymmetric synthesis of 3,3-disubstituted 1-indanones, see: Shintani, R.; Takatsu, K.; Hayashi, T. Angew. Chem. 2007, 119, 3809;
  • 21
  • 23
    • 0034249671 scopus 로고    scopus 로고
    • For reviews on Heck-Mizoroki cross-coupling reactions, see: a
    • For reviews on Heck-Mizoroki cross-coupling reactions, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
    • (2000) Chem. Rev , vol.100 , pp. 3009
    • Beletskaya, I.P.1    Cheprakov, A.V.2
  • 24
    • 4644349037 scopus 로고    scopus 로고
    • Cross-Coupling of Organyl Halides with Alkenes - The Heck Reaction
    • de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim, Germany
    • (b) Bräse, S.; de Meijere, A. Cross-Coupling of Organyl Halides with Alkenes - The Heck Reaction. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 217-315.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.1 , pp. 217-315
    • Bräse, S.1    de Meijere, A.2
  • 25
    • 36648999956 scopus 로고    scopus 로고
    • This reaction type can formally be classified as a catalyzed asymmetric arylation reaction. For a review, see: Bolm, C, Hildebrand, J. P, Muñiz, K, Hermanns, N. Angew. Chem. 2001, 113, 3382;
    • This reaction type can formally be classified as a catalyzed asymmetric arylation reaction. For a review, see: Bolm, C.; Hildebrand, J. P.; Muñiz, K.; Hermanns, N. Angew. Chem. 2001, 113, 3382;
  • 27
    • 36649015725 scopus 로고    scopus 로고
    • 3e
    • 3e
  • 28
    • 36649035201 scopus 로고    scopus 로고
    • Although the results obtained with the nonaflate 1a (X, ONf) and the triflate 1a (X, OTf) were identical, the easier handling of the nonaflate made it the substrate of choice
    • Although the results obtained with the nonaflate 1a (X = ONf) and the triflate 1a (X = OTf) were identical, the easier handling of the nonaflate made it the substrate of choice.
  • 34
    • 36649022995 scopus 로고    scopus 로고
    • Aventis Pharma SA; Preparation of 3-arylindan-1-ones as inhibitors of tubulin polymerization and their composition for treatment of cancer. FR 2838432, A1, October 17, 2003.
    • Aventis Pharma SA; Preparation of 3-arylindan-1-ones as inhibitors of tubulin polymerization and their composition for treatment of cancer. FR 2838432, A1, October 17, 2003.
  • 35
    • 84987458578 scopus 로고    scopus 로고
    • A single report on the generation of racemic 3a in 1% yield by gas-flow thermolysis has been reported: Koller, M.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 560.
    • A single report on the generation of racemic 3a in 1% yield by gas-flow thermolysis has been reported: Koller, M.; Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1986, 69, 560.
  • 43
    • 0001379350 scopus 로고    scopus 로고
    • Complexation of a tertiary amine with palladium(II) followed by metal insertion and subsequent β-hydride elimination has been described before: (a) Konopelski, J. P.; Chu, K. S.; Negrete, G. R. J. Org. Chem. 1991, 56, 1355.
    • Complexation of a tertiary amine with palladium(II) followed by metal insertion and subsequent β-hydride elimination has been described before: (a) Konopelski, J. P.; Chu, K. S.; Negrete, G. R. J. Org. Chem. 1991, 56, 1355.
  • 48
    • 36649025602 scopus 로고    scopus 로고
    • Attempts to synthesize the Eschemoser salt V independently did not meet with success
    • Attempts to synthesize the Eschemoser salt V independently did not meet with success.
  • 49
    • 33749528548 scopus 로고    scopus 로고
    • A similar Mannich reaction with cyclic enones and elimination of the amino group has been reported before: Porzelle, A, Williams, C. M. Synthesis 2006, 3025
    • A similar Mannich reaction with cyclic enones and elimination of the amino group has been reported before: Porzelle, A.; Williams, C. M. Synthesis 2006, 3025.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.