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Volumn 61, Issue 8, 2005, Pages 2217-2231

Highly chemoselective hydrogenation method using novel finely dispersed palladium catalyst on silk-fibroin: Its preparation and activity

Author keywords

Chemoselective; Hydrogenation; Palladium catalyst; Silk fibroin

Indexed keywords

ACETYLENE DERIVATIVE; ALDEHYDE; ALKENE DERIVATIVE; AROMATIC COMPOUND; AZIDE; ESTER DERIVATIVE; HALIDE; KETONE DERIVATIVE; PALLADIUM; SILK FIBROIN;

EID: 13444310678     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.11.080     Document Type: Article
Times cited : (106)

References (55)
  • 8
    • 13444254953 scopus 로고    scopus 로고
    • note
    • Commercially available from Wako Pure Chemical Industires, Ltd. (Japan) as palladium-activated carbon ethylene diamine complex (Pd 5%) [5% Pd/C(en), 163-21441 and 169-21443].
  • 9
    • 0004238250 scopus 로고    scopus 로고
    • M. Lewin E.M. Pearce 2nd ed. Marcel Dekker New York
    • R.M. Robson M. Lewin E.M. Pearce Handbook of Fiber Chemistry 2nd ed. 1998 Marcel Dekker New York
    • (1998) Handbook of Fiber Chemistry
    • Robson, R.M.1
  • 10
    • 0001544341 scopus 로고
    • F. Lucas Nature 210 1966 952 953
    • (1966) Nature , vol.210 , pp. 952-953
    • Lucas, F.1
  • 30
    • 0007688515 scopus 로고
    • (a) Kuzuhara et al. have reported the chemoselective hydrogenation of an azido group in the presence of an aliphatic N-Cbz protective group using Raney Ni, which must be added into the reaction mixture in small portions with careful monitoring to avoid cleavage of the N-Cbz group. H. Kuzuhara, O. Mori, and S. Emoto Tetrahedron Lett. 1976 379 382
    • (1976) Tetrahedron Lett. , pp. 379-382
    • Kuzuhara, H.1    Mori, O.2    Emoto, S.3
  • 31
    • 0033820408 scopus 로고    scopus 로고
    • (b) Shinada and Ohfune et al. reported a chemoselective hydrogenation of olefin and benzyl ester functionalities in the presence of N-Cbz and benzyl ether protective groups using Pd/C while the stability of the N-Cbz group under the conditions was time-dependent. T. Shinada, K. Hayashi, Y. Yoshida, and Y. Ohfune Synlett 2000 1506 1508
    • (2000) Synlett , pp. 1506-1508
    • Shinada, T.1    Hayashi, K.2    Yoshida, Y.3    Ohfune, Y.4
  • 33
    • 0037424037 scopus 로고    scopus 로고
    • We have quite recently reported the frequent and unexpected cleavage of tert-butyldimethylsilyl (TBDMS) ethers to form the parent alcohols under mild hydrogenation conditions using 10% Pd/C in MeOH although TBDMS ethers have been believed to be stable under hydrogenation conditions. Furthermore, we have reported a remarkable solvent effect toward the Pd/C-catalyzed cleavage of TBDMS and triethylsilyl (TES) ethers and it was applied to the development of a chemoselective hydrogenation method for olefin, benzyl ether and acetylene functionalities distinguishing from the TBDMS and TES protective groups of a hydroxy group by the employment of EtOAc or MeCN as a solvent. See: H. Sajiki, T. Ikawa, K. Hattori, and K. Hirota Chem. Commun. 2003 654 655
    • (2003) Chem. Commun. , pp. 654-655
    • Sajiki, H.1    Ikawa, T.2    Hattori, K.3    Hirota, K.4
  • 36
    • 33845278094 scopus 로고
    • Quite a few methods to maintain the benzyl ester intact during a synthetic process involving conjugate reduction (non-hydrogenation) steps have been reported. (a) W.S. Mathoney, D.M. Brestensky, and J.M. Stryker J. Am. Chem. Soc. 110 1988 291 293
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 291-293
    • Mathoney, W.S.1    Brestensky, D.M.2    Stryker, J.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.