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Volumn 130, Issue 41, 2008, Pages 13528-13529

Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-Furyl)carbene complexes

Author keywords

[No Author keywords available]

Indexed keywords

(2 FURYL)CARBENE COMPLEX; CARBENOID; COPPER; ESTER DERIVATIVE; FURAN DERIVATIVE; PROPARGYLIC ESTER; UNCLASSIFIED DRUG;

EID: 53849147913     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8058342     Document Type: Article
Times cited : (114)

References (30)
  • 6
    • 53249152128 scopus 로고    scopus 로고
    • For a recent report on gold intermediates, see: b
    • For a recent report on gold intermediates, see: (b) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2008, 47, 6754.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 6754
    • Hashmi, A.S.K.1
  • 8
    • 1942504521 scopus 로고    scopus 로고
    • Selected references showing the prominent role of the furan ring due to its presence in many natural and biologically active products and to its potential as synthetic intermediate: (a) Hou, X. L, Yang, Z, Wong, H. N. C. in Progress in Heterocyclic Chemistry; Gribble, G. W, Gilchrist, T. L. Eds, Pergamon: Oxford, U.K, 2003; 15, p 167
    • Selected references showing the prominent role of the furan ring due to its presence in many natural and biologically active products and to its potential as synthetic intermediate: (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. in Progress in Heterocyclic Chemistry; Gribble, G. W.; Gilchrist, T. L. Eds.; Pergamon: Oxford, U.K., 2003; Vol. 15, p 167.
  • 9
    • 0001176061 scopus 로고    scopus 로고
    • Katrizky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Elsevier: Oxford, U.K
    • (b) Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford, U.K., 1997; Vol. 2, p 395.
    • (1997) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 395
    • Keay, B.A.1    Dibble, P.W.2
  • 11
    • 33744802336 scopus 로고    scopus 로고
    • For an overview covering the difficulties in accessing polysubstituted furans, see
    • For an overview covering the difficulties in accessing polysubstituted furans, see: Kirch, S. F. Org. Biomol. Chem. 2006, 4, 2076.
    • (2006) Org. Biomol. Chem , vol.4 , pp. 2076
    • Kirch, S.F.1
  • 12
    • 0037429821 scopus 로고    scopus 로고
    • For a review on the synthetic applications of copper(I) carbene complexes resulting from copper(I)-catalyzed decomposition of diazoesters, see: Kirmse, W. Angew. Chem., Int. Ed. 2003, 42, 1088.
    • For a review on the synthetic applications of copper(I) carbene complexes resulting from copper(I)-catalyzed decomposition of diazoesters, see: Kirmse, W. Angew. Chem., Int. Ed. 2003, 42, 1088.
  • 13
    • 0037181027 scopus 로고    scopus 로고
    • The generation of a Cu(I) isoindazolylcarbene by CuCl-catalyzed azo-enyne cyclization and the cyclopropanation to tetramethylethene has been reported: (a) Kimball, D. B.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572.
    • The generation of a Cu(I) isoindazolylcarbene by CuCl-catalyzed azo-enyne cyclization and the cyclopropanation to tetramethylethene has been reported: (a) Kimball, D. B.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572.
  • 15
    • 0001323454 scopus 로고    scopus 로고
    • The copper-catalyzed Si-H insertion into diazoesters and ketones has been reported: Bagheri, V.; Doyle, M. P.; Taunton, J.; Claxton, E. E. J. Org. Chem. 1988, 53, 6158.
    • The copper-catalyzed Si-H insertion into diazoesters and ketones has been reported: Bagheri, V.; Doyle, M. P.; Taunton, J.; Claxton, E. E. J. Org. Chem. 1988, 53, 6158.
  • 16
    • 53849149177 scopus 로고    scopus 로고
    • 2, room temp) in the absence of triethylsilane 3a afforded the corresponding dimer 2b in 85% yield.
    • 2, room temp) in the absence of triethylsilane 3a afforded the corresponding dimer 2b in 85% yield.
  • 17
    • 0001031980 scopus 로고    scopus 로고
    • The extremely ease with which most transition metal alkyl carbenes suffer β-hydride elimination is well documented, see for example: (a) Taber, D. F, Herr, R. J, Pack, S. K, Geremia, J. M. J. Org. Chem. 1996, 61, 2908 In some cases the use of low reaction temperatures and sterically demanding carboxylates proved to be useful in order to avoid β-hydride elimination
    • The extremely ease with which most transition metal alkyl carbenes suffer β-hydride elimination is well documented, see for example: (a) Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908 In some cases the use of low reaction temperatures and sterically demanding carboxylates proved to be useful in order to avoid β-hydride elimination.
  • 18
    • 33846113394 scopus 로고    scopus 로고
    • For recent successful Rh(I)-catalyzed reactions of α-alkyl-α- diazoesters with alkynes and alkenes, see: (b) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22.
    • For recent successful Rh(I)-catalyzed reactions of α-alkyl-α- diazoesters with alkynes and alkenes, see: (b) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22.
  • 20
    • 53849143808 scopus 로고    scopus 로고
    • In all the cases examined, the dimer resulting from the competing carbene ligand dimerization was detected in less than 10% yield
    • In all the cases examined, the dimer resulting from the competing carbene ligand dimerization was detected in less than 10% yield.
  • 21
    • 53849132940 scopus 로고    scopus 로고
    • 3SnH resulted only in extensive decomposition and no furane derivative was ever isolated.
    • 3SnH resulted only in extensive decomposition and no furane derivative was ever isolated.
  • 22
    • 53849109383 scopus 로고    scopus 로고
    • In this coupling process CuBr proved to be superior to the cationic complex in terms of chemical yield
    • In this coupling process CuBr proved to be superior to the cationic complex in terms of chemical yield.
  • 23
    • 53849122514 scopus 로고    scopus 로고
    • During the study of the optimization and scope of this process we found that the treatment of diyne 1d with diethyl diazomalonate in the presence of CuBr (5 mol , did not produce the heterocoupling product. In this case the diazo derivative acts just as a modulating ligand giving rise to the Knoevenagel adduct 9 in 65% yield. Furthermore, the treatment of compound 9 with triethylsilane 3a, Cu(CH3CN)4][BF 4, 5 mol, CH2Cl2, room temp) or EDA (CuBr, 5 mol, CH2Cl2, room temp) afforded the furan derivatives 4e (92, and 7b 89, respectively, Chemical Equation Presented
    • 2, room temp) afforded the furan derivatives 4e (92%) and 7b (89%), respectively. (Chemical Equation Presented)
  • 24
    • 34248597739 scopus 로고    scopus 로고
    • The oxidation of the gold(I) carbene intermediate formed by 1,2-pivaloyloxy rearrangement of propargylic esters has been achieved using sulfoxides as the stoichiometric oxidants: Witham, C. A.; Mauleón, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
    • The oxidation of the gold(I) carbene intermediate formed by 1,2-pivaloyloxy rearrangement of propargylic esters has been achieved using sulfoxides as the stoichiometric oxidants: Witham, C. A.; Mauleón, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
  • 25
    • 53849136113 scopus 로고    scopus 로고
    • The metal-catalyzed reactions of bis-propargylic esters are extremely rare. For an isolated example involving (1,1-diethynylmetyl) acetates, see: Kato, K.; Teraguchi, R.; Kusakabe, T.; Motodate, S.; Yamamura, S.; Mochida, T.; Akita, H. Synlett 2007, 63.
    • The metal-catalyzed reactions of bis-propargylic esters are extremely rare. For an isolated example involving (1,1-diethynylmetyl) acetates, see: Kato, K.; Teraguchi, R.; Kusakabe, T.; Motodate, S.; Yamamura, S.; Mochida, T.; Akita, H. Synlett 2007, 63.
  • 26
    • 0345580714 scopus 로고    scopus 로고
    • Nonmetal 2-furfurylidenes from diazocompounds cannot be trapped due to rapid ring-opening rearrangement; see: (a) Sun, Y.; Wong, M. W. J. Org. Chem. 1999, 64, 9170
    • Nonmetal 2-furfurylidenes from diazocompounds cannot be trapped due to rapid ring-opening rearrangement; see: (a) Sun, Y.; Wong, M. W. J. Org. Chem. 1999, 64, 9170
  • 27
    • 0033568246 scopus 로고    scopus 로고
    • For successful trapping of 2-furyl carbenes derived from photocyclization of 1,2-diketones conjugated with eneyne, see: b
    • For successful trapping of 2-furyl carbenes derived from photocyclization of 1,2-diketones conjugated with eneyne, see: (b) Nakatani, K.; Adachi, K.; Tanabe, K.; Saito, I. J. Am. Chem. Soc. 1999, 121, 8221.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 8221
    • Nakatani, K.1    Adachi, K.2    Tanabe, K.3    Saito, I.4
  • 28
    • 0037094001 scopus 로고    scopus 로고
    • For generation of 2-furylcarbenes of other transition metals by cyclization of 1-buten-3-ynylketones, see: a
    • For generation of 2-furylcarbenes of other transition metals by cyclization of 1-buten-3-ynylketones, see: (a) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 5260
    • Miki, K.1    Nishino, F.2    Ohe, K.3    Uemura, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.