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Volumn , Issue 20, 2007, Pages 3201-3205

Use of the composite material RuO2/BaTi4O9 as an environmentally benign solid catalyst for the oxidative cleavage of olefins

Author keywords

Cleavage; Green chemistry; Heterogeneous catalysis; Oxidation; Ruthenium

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; BARIUM; CARBOXYLIC ACID DERIVATIVE; KETONE DERIVATIVE; PERIODATE SODIUM; RUTHENIUM; TITANIUM;

EID: 37749049399     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992378     Document Type: Article
Times cited : (20)

References (26)
  • 2
    • 0141741232 scopus 로고    scopus 로고
    • For recent works describing transition-metal-mediated cleavage with Os reagent, see: a
    • For recent works describing transition-metal-mediated cleavage with Os reagent, see: (a) Ley, S. V.; Ramarao, C.; Lee, A.; Ostergaard, N.; Smith, S. C.; Shirley, I. M. Org. Lett. 2003, 5, 185.
    • (2003) Org. Lett , vol.5 , pp. 185
    • Ley, S.V.1    Ramarao, C.2    Lee, A.3    Ostergaard, N.4    Smith, S.C.5    Shirley, I.M.6
  • 4
    • 33644784644 scopus 로고    scopus 로고
    • With AuCl reagent, see: Xing, D, Guan, B, Cai, G, Fang, Z, Yang, L, Shi, Z. Org. Lett. 2006, 8, 693
    • (c) With AuCl reagent, see: Xing, D.; Guan, B.; Cai, G.; Fang, Z.; Yang, L.; Shi, Z. Org. Lett. 2006, 8, 693.
  • 6
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    • For recent typical examples, see: a
    • For recent typical examples, see: (a) Kim, W.; Park, I.; Park, J. Org. Lett. 2006, 8, 2543.
    • (2006) Org. Lett , vol.8 , pp. 2543
    • Kim, W.1    Park, I.2    Park, J.3
  • 10
    • 4644293702 scopus 로고    scopus 로고
    • For an excellent work detailing control of the oxidation stage with immobilized Ru species, see
    • For an excellent work detailing control of the oxidation stage with immobilized Ru species, see: Ho, C.; Yu, W.; Che, C. Angew. Chem. Int. Ed. 2004, 43, 3303.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3303
    • Ho, C.1    Yu, W.2    Che, C.3
  • 15
    • 0035854317 scopus 로고    scopus 로고
    • 3 leading to aldehyde, see: (a) Yang, D.; Zhang, C. J. Org. Chem. 2001, 66, 4814.
    • 3 leading to aldehyde, see: (a) Yang, D.; Zhang, C. J. Org. Chem. 2001, 66, 4814.
  • 16
    • 33645501568 scopus 로고    scopus 로고
    • 3 leading to diol, see: (b) Tiwari, P.; Misra, A. K. J. Org. Chem. 2006, 71, 2911.
    • 3 leading to diol, see: (b) Tiwari, P.; Misra, A. K. J. Org. Chem. 2006, 71, 2911.
  • 19
    • 9344260283 scopus 로고    scopus 로고
    • 3 leading to acyloin, see: Plietker, B. J. Org. Chem. 2004, 69, 8287.
    • 3 leading to acyloin, see: Plietker, B. J. Org. Chem. 2004, 69, 8287.
  • 20
    • 33846649589 scopus 로고    scopus 로고
    • The sugar derivatives 8, 11 and 13 were prepared from D-ribose, D-arabinose and D-xylose, respectively, according to the literature, followed by usual acetylation: (a) Shing, T. K. M.; Wong, W. F.; Ikeno, T.; Yamada, T. Org. Lett. 2007, 9, 207.
    • The sugar derivatives 8, 11 and 13 were prepared from D-ribose, D-arabinose and D-xylose, respectively, according to the literature, followed by usual acetylation: (a) Shing, T. K. M.; Wong, W. F.; Ikeno, T.; Yamada, T. Org. Lett. 2007, 9, 207.
  • 23
    • 37749041099 scopus 로고    scopus 로고
    • The acetate 15 was synthesized by reaction of the aldehyde 19 and allyl Grignard reagent, followed by acetylation as illustrated in (Chemical Equation Presented) Scheme 4. For preparation of the intermediate aldehyde 19, see ref. 10a and: Calinaud, P.; Gelas, J. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1996, p15.
    • (d) The acetate 15 was synthesized by reaction of the aldehyde 19 and allyl Grignard reagent, followed by acetylation as illustrated in (Chemical Equation Presented) Scheme 4. For preparation of the intermediate aldehyde 19, see ref. 10a and: Calinaud, P.; Gelas, J. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1996, p15.
  • 24
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    • The diacetonide 17 is readily accessible from D-mannose: Shing, T. K. M.; Wong, W. F.; Cheng, H. M.; Kwok, W. S.; So, K. H. Org. Lett. 2007, 9, 753.
    • (e) The diacetonide 17 is readily accessible from D-mannose: Shing, T. K. M.; Wong, W. F.; Cheng, H. M.; Kwok, W. S.; So, K. H. Org. Lett. 2007, 9, 753.
  • 25
    • 37749021914 scopus 로고    scopus 로고
    • 2O. Filtrates were extracted with EtOAc and the organic layer was dried and concentrated. The residue was then chromatographed on silica gel to give the product.
    • 2O. Filtrates were extracted with EtOAc and the organic layer was dried and concentrated. The residue was then chromatographed on silica gel to give the product.
  • 26
    • 37749018447 scopus 로고    scopus 로고
    • 2a: 1H NMR (300 MHz, CDCl3, δ, 0.85 (t, J, 7.6 Hz, 3 H, 1.25 (t, J, 7.2 Hz, 6 H, 2.05 (q, J, 7.6 Hz, 2 H, 2.17 (s, 3 H, 3.10 (s, 2 H, 4.19 (q, J, 7.0 Hz, 4 H, 13C NMR (75 MHz, CDCl3, δ, 8.8, 13.7, 26.2, 30.0, 45.2, 55.6, 61.1, 170.5, 204.9. 2b: a mixture of separable diastereomers in a ratio of ca. 4:1. Major product: 1H NMR (500 MHz, CDCl 3, δ, 1.04 (d, J, 6.4 Hz, 3 H, 1.43 (ddd, J, 3.3, 13.1, 26.3 Hz, 1 H, 1.73 (ddd, J, 3.4, 13.1, 25.6 Hz, 1 H, 2.19 (s, 3 H, 2.08-2.25 (m, 2 H, 2.35-2.45 (m, 1 H, 2.45-2.52 (m, 2 H, 2.77-2.86 (m, 1 H, 13C NMR (126 MHz, CDCl3, δ, 14.2, 27.7, 28.2, 34.5, 42.6, 44.5, 52.1, 208.1, 211.4. Minor product: 1H NMR (500 MHz, CDCl3, δ, 1.09 (d, J, 7.0 Hz, 3 H, 1.50-1.58 (m, 1 H, 1.91-2.10 (m, 3 H, 2.18 s, 3 H, 2.30-2.42
    • 3): δ = 1.27


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.