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Volumn 51, Issue 24, 2012, Pages 5847-5851

Enol acetal synthesis through carbenoid C-H insertion into tetrahydrofuran catalyzed by CpRu complexes

Author keywords

C H insertion; C O coupling; diazo compounds; enol acetals; tetrahydrofurans

Indexed keywords

ACETAL SYNTHESIS; C-C BOND FORMATION; C-H INSERTION; CARBENOIDS; DIAZO COMPOUNDS; DIIMINE LIGAND; ENOL ACETALS; KETO ESTER; TETRA-HYDROFURAN; TETRAHYDROFURANS;

EID: 84861845792     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201541     Document Type: Article
Times cited : (42)

References (84)
  • 10
    • 84861871018 scopus 로고    scopus 로고
    • α-Functionalization of THF derivatives is also feasible through free-radical and other metal-catalyzed processes
    • α-Functionalization of THF derivatives is also feasible through free-radical and other metal-catalyzed processes
  • 35
    • 77953488071 scopus 로고    scopus 로고
    • G. Maas, Angew. Chem. 2009, 121, 8332-8341
    • (2009) Angew. Chem. , vol.121 , pp. 8332-8341
    • Maas, G.1
  • 36
    • 70350034042 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 8186-8195; see also
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 8186-8195
  • 53
    • 77957340598 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 7253-7256
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 7253-7256
  • 55
    • 79960903370 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 7308-7311.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7308-7311
  • 61
    • 0002930470 scopus 로고    scopus 로고
    • CpRu complexes with cyclooctadiene and diphosphine ligands, known to catalyze the decomposition of certain diazo derivatives, were unreactive in the titled chemistry:, W. Baratta, A. DelZotto, Rigo, Chem. Commun. 1997, 2163-2164
    • (1997) Chem. Commun. , pp. 2163-2164
    • Baratta, W.1    Delzotto, A.2    Rigo, P.3
  • 64
    • 84861874795 scopus 로고    scopus 로고
    • Without ligand, only 12 % conversion is observed and polymerization of THF occurs
    • Without ligand, only 12 % conversion is observed and polymerization of THF occurs.
  • 65
    • 14844353342 scopus 로고
    • 1HNMR signals at 5.66 (d, J=4Hz, OCHO) and 5.32 (s, C-CH) ppm that are at quite higher frequency than the most deshielded proton of 4 a (m, =4.43ppm). The configuration of the double bond is readily determined by a NOESY experiment; see:, R. Bihovsky, M. U. Kumar, S. Ding, A. Goyal, J. Org. Chem. 1989, 54, 4291-4293
    • (1989) J. Org. Chem. , vol.54 , pp. 4291-4293
    • Bihovsky, R.1    Kumar, M.U.2    Ding, S.3    Goyal, A.4
  • 73
    • 36849042274 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8979-8982.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8979-8982
  • 75
    • 0242354877 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 5066-5068.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5066-5068
  • 76
    • 84861877626 scopus 로고    scopus 로고
    • Moderate yields are often due to the volatility of the compounds
    • Moderate yields are often due to the volatility of the compounds.
  • 77
    • 84861897952 scopus 로고    scopus 로고
    • After 48h, only 25 % conversion of 1 l into the dimer product was observed
    • After 48h, only 25 % conversion of 1 l into the dimer product was observed.
  • 80
    • 77955359154 scopus 로고    scopus 로고
    • An alternative hydride abstraction mechanism can be considered:, H. T. Bonge, T. Hansen, Eur. J. Org. Chem. 2010, 4355-4359.
    • (2010) Eur. J. Org. Chem. , pp. 4355-4359
    • Bonge, H.T.1    Hansen, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.