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Volumn , Issue 15, 2010, Pages 2861-2866

An efficient iron-catalyzed carbon-carbon single-bond cleavage via retro-claisen condensation: A mild and convenient approach to synthesize a variety of esters or ketones

Author keywords

Cleavage reactions; Esters; Iron; Ketones; Nucleophilic addition

Indexed keywords


EID: 77952199786     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000128     Document Type: Article
Times cited : (77)

References (120)
  • 1
    • 44349129755 scopus 로고    scopus 로고
    • For a general review on iron catalysis, see: a
    • For a general review on iron catalysis, see: a) A. Correa, O. G. Mancheño, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-1117;
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1108-1117
    • Correa, A.1    Mancheño, O.G.2    Bolm, C.3
  • 3
    • 50049109778 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 3317-3321;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3317-3321
  • 7
  • 12
    • 34250882685 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 3718-3721;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3718-3721
  • 17
    • 4644283019 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed, 2004, 43, 4225-4228;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 4225-4228
  • 19
    • 0344845085 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 5487-5489;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5487-5489
  • 21
    • 34548356423 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 6505-6507;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 6505-6507
  • 23
    • 54749149062 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7497-7500.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7497-7500
  • 26
    • 35048886101 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7360-7363;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7360-7363
  • 32
    • 42449118890 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed, 2008, 47, 2497-2501;
    • (2008) , vol.47 , pp. 2497-2501
    • Ed, A.C.Int.1
  • 35
    • 34948835849 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7293-7296;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7293-7296
  • 43
    • 44349129755 scopus 로고    scopus 로고
    • For general reviews on iron catalysis, see: a
    • For general reviews on iron catalysis, see: a) A. Correa, O. G. Mancheno, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-1117;
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1108-1117
    • Correa, A.1    Mancheno, O.G.2    Bolm, C.3
  • 45
    • 50049109778 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 3317-3321.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3317-3321
  • 46
    • 34547873501 scopus 로고    scopus 로고
    • For recent papers on iron catalysis, see: a
    • For recent papers on iron catalysis, see: a) T. Hatakeyama, M. Nakamura, J. Am. Chem. Soc. 2007, 129, 9844-9845;
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9844-9845
    • Hatakeyama, T.1    Nakamura, M.2
  • 48
    • 34548356423 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 6505-6507;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 6505-6507
  • 50
    • 54749149062 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 7497-7500;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7497-7500
  • 52
    • 41249092534 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 1305-1307;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 1305-1307
  • 56
    • 17044409192 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1654-1657;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1654-1657
  • 60
    • 4644283257 scopus 로고    scopus 로고
    • For iron-catalyzed reactions reported by the group of Bolm, see: a
    • For iron-catalyzed reactions reported by the group of Bolm, see: a) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-5647;
    • (2003) Angew. Chem. , vol.115 , pp. 5645-5647
    • Legros, J.1    Bolm, C.2
  • 61
    • 0344845085 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 5487-5489;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5487-5489
  • 63
    • 44349129755 scopus 로고    scopus 로고
    • a For a review on iron-catalyzed carbon-heteroatom bondformation reactions, see
    • a) For a review on iron-catalyzed carbon-heteroatom bondformation reactions, see: A. Correa, O. G. Mancheño, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-1117;
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1108-1117
    • Correa, A.1    Mancheño, O.G.2    Bolm, C.3
  • 68
    • 70349783568 scopus 로고    scopus 로고
    • for iron-catalyzed carbon-heteroatom bond formation contaminated by copper, see
    • f) for iron-catalyzed carbon-heteroatom bond formation contaminated by copper, see: S. L. Buchwald, C. Bolm, Angew. Chem. Int. Ed. 2009, 48, 5586-5587.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5586-5587
    • Buchwald, S.L.1    Bolm, C.2
  • 69
    • 70350142896 scopus 로고    scopus 로고
    • a For a review on iron-catalyzed oxidative coupling, see
    • a) For a review on iron-catalyzed oxidative coupling, see: A. A. O. Sarhan, C. Bolm, Chem. Soc. Rev. 2009, 38, 2730-2744;
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 2730-2744
    • Sarhan, A.A.O.1    Bolm, C.2
  • 81
    • 70349782138 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 2969-2972.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2969-2972
  • 83
    • 77949289987 scopus 로고    scopus 로고
    • 3-catalyzed synthesis of heterocycles, see: a
    • 3-catalyzed synthesis of heterocycles, see: a) S. Maiti, ' S. Biswas, U. Jana, J. Org. Chem. 2010, 75, 1674-1683;
    • (2010) J. Org. Chem. , vol.75 , pp. 1674-1683
    • Maiti, S.1    Biswas, S.2    Jana, U.3
  • 90
    • 66149143042 scopus 로고    scopus 로고
    • For iron-catalyzed activation of alcohols reported by our group, see: a
    • For iron-catalyzed activation of alcohols reported by our group, see: a) S. Biswas, S. Maiti, U. Jana, Eur. J. Org. Chem. 2009, 2354-2359;
    • (2009) Eur. J. Org. Chem. , pp. 2354-2359
    • Biswas, S.1    Maiti, S.2    Jana, U.3
  • 111
    • 35349007000 scopus 로고    scopus 로고
    • For a recent report on the retro-Claisen condensation reaction, see: and references cited therein.
    • For a recent report on the retro-Claisen condensation reaction, see: A. Kawata, K. Takata, Y. Kuninobu, K. Takai, Angew. Chem. Int. Ed. 2007, 46, 7793-7795 and references cited therein.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7793-7795
    • Kawata, A.1    Takata, K.2    Kuninobu, Y.3    Takai, K.4
  • 114
    • 62249203584 scopus 로고    scopus 로고
    • for recent oxidative esterifications using iron, see
    • c) for recent oxidative esterifications using iron, see: X.-F. Wu, C. Darcel, Eur. J. Org. Chem. 2009, 1144-1147;
    • (2009) Eur. J. Org. Chem. , pp. 1144-1147
    • Wu, X.-F.1    Darcel, C.2
  • 115
    • 53849129886 scopus 로고    scopus 로고
    • for a recent review based on the one-pot oxidative esterification of aldehyde, see: and references cited therein
    • d) for a recent review based on the one-pot oxidative esterification of aldehyde, see: K. Ekoue-Kovi, C. Wolf, Chem. Eur. J. 2008, 14, 6302-6315 and references cited therein;
    • (2008) Chem. Eur. J. , vol.14 , pp. 6302-6315
    • Ekoue-Kovi, K.1    Wolf, C.2
  • 116
    • 33846263996 scopus 로고    scopus 로고
    • for copper-catalyzed oxidative esterification, see
    • e) for copper-catalyzed oxidative esterification, see: W.-J. Yoo, C.-J. Li, Tetrahedron Lett. 2007, 48, 1033-1035.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 1033-1035
    • Yoo, W.-J.1    Li, C.-J.2
  • 117
    • 77952206870 scopus 로고    scopus 로고
    • note
    • The formation of carboxylic acid 3m can be explained from retro-Claisen reaction of 2-acetylcyclopentanone with tert-butyl alcohol followed by alkyl-oxygen bond cleavage of tert-hutyl ester under the same reaction conditions. Moreover, in situ generation of water from iron-salt-catalyzed dehydration of tert/-butyl alcohol through an El mechanism followed by retroClaisen condensation of 2-acetylcyclopentanone with in situ generated water also can be considered.
  • 120
    • 69549120370 scopus 로고    scopus 로고
    • For iron-catalyzed carbon-carbon bond-cleavage reactions, see, and references cited therein.
    • For iron-catalyzed carbon-carbon bond-cleavage reactions, see, H. Li, J. Yang, Y. Liu, Y. Li, J. Org. Chem. 2009, 74, 6797-6801 and references cited therein.
    • (2009) J. Org. Chem. , vol.74 , pp. 6797-6801
    • Li, H.1    Yang, J.2    Liu, Y.3    Li, Y.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.