메뉴 건너뛰기




Volumn 50, Issue 7, 2011, Pages 1678-1682

Lewis acid activated synthesis of highly substituted cyclopentanes by the n-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters

Author keywords

asymmetric catalysis; asymmetric synthesis; homoenolates; Lewis acids; N heterocyclic carbenes

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; HOMOENOLATES; LEWIS ACIDS; N-HETEROCYCLIC CARBENES;

EID: 79851496680     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201005908     Document Type: Article
Times cited : (144)

References (71)
  • 16
    • 79851477557 scopus 로고    scopus 로고
    • (Eds.: M. T. Reetz, B. List, S. Jaroch, H. Weinmann), Springer, Heidelberg
    • K. Zeitler, in Organocatalysis (Eds.:, M. T. Reetz, B. List, S. Jaroch, H. Weinmann,), Springer, Heidelberg, 2008, pp. 183-206
    • (2008) Organocatalysis , pp. 183-206
    • Zeitler, K.1
  • 17
    • 79851498771 scopus 로고    scopus 로고
    • (Eds.: M. T. Reetz, B. List, S. Jaroch, H. Weinmann), Springer, Heidelberg
    • F. Glorius, K. Hirano, in Organocatalysis (Eds.:, M. T. Reetz, B. List, S. Jaroch, H. Weinmann,), Springer, Heidelberg, 2008, pp. 183-206
    • (2008) Organocatalysis , pp. 183-206
    • Glorius, F.1    Hirano, K.2
  • 21
    • 56549104231 scopus 로고    scopus 로고
    • For a recent review of methodology for the generation of homoenolates with NHCs, see
    • For a recent review of methodology for the generation of homoenolates with NHCs, see:, V. Nair, S. Vellalath, B. P. Babu, Chem. Soc. Rev. 2008, 37, 2691.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 2691
    • Nair, V.1    Vellalath, S.2    Babu, B.P.3
  • 38
    • 33947696588 scopus 로고    scopus 로고
    • For an enantioselective variant of the NHC reaction described by Nair et al., see
    • For an enantioselective variant of the NHC reaction described by Nair et al., see:, P.-C. Chiang, J. Kaeobamrung, J. W. Bode, J. Am. Chem. Soc. 2007, 129, 3520.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 3520
    • Chiang, P.-C.1    Kaeobamrung, J.2    Bode, J.W.3
  • 39
    • 32644452625 scopus 로고    scopus 로고
    • For NHC-homoenolate additions to 1,2-dicarbonyl compounds, see
    • For NHC-homoenolate additions to 1,2-dicarbonyl compounds, see:, V. Nair, S. Vellalath, M. Poonoth, R. Mohan, E. Suresh, Org. Lett. 2006, 8, 507.
    • (2006) Org. Lett. , vol.8 , pp. 507
    • Nair, V.1    Vellalath, S.2    Poonoth, M.3    Mohan, R.4    Suresh, E.5
  • 41
    • 77951079080 scopus 로고    scopus 로고
    • for other examples of NHC-metal cooperative catalysis, see
    • B. Cardinal-David, D. E. A. Raup, K. A. Scheidt, J. Am. Chem. Soc. 2010, 132, 5345; for other examples of NHC-metal cooperative catalysis, see
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 5345
    • Cardinal-David, B.1    Raup, D.E.A.2    Scheidt, K.A.3
  • 61
    • 79851490364 scopus 로고    scopus 로고
    • The absolute and relative configuration were determined by X-ray crystallography for compound 4 (see Tablea 2, entrya 2) and the others were assigned by analogy (see the Supporting Information). The relative configuration of the minor diastereomer 29 was determined by X-ray crystallography and others were assigned by analogy (see the Supporting Information). CCDCa 793381 (4) and 793382 (29) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • The absolute and relative configuration were determined by X-ray crystallography for compound 4 (see Tablea 2, entrya 2) and the others were assigned by analogy (see the Supporting Information). The relative configuration of the minor diastereomer 29 was determined by X-ray crystallography and others were assigned by analogy (see the Supporting Information). CCDCa 793381 (4) and 793382 (29) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
  • 62
    • 79851488910 scopus 로고    scopus 로고
    • The minor positive influence that 2-propanol has on the stereoselectivity is currently under investigation
    • The minor positive influence that 2-propanol has on the stereoselectivity is currently under investigation.
  • 63
    • 79851484969 scopus 로고    scopus 로고
    • A decrease in the catalyst loading (to 5 and 10a mol%) resulted in incomplete conversion (50 and 80%, respectively) after 48a h
    • A decrease in the catalyst loading (to 5 and 10a mol%) resulted in incomplete conversion (50 and 80%, respectively) after 48a h.
  • 64
    • 79851469909 scopus 로고    scopus 로고
    • 8]THF, no detectable differences were observed in the signals relative to those in the spectra of the starting material. Efforts are currently under way to understand the full role of the Lewis acid in these cooperative carbene catalytic processes
    • 8]THF, no detectable differences were observed in the signals relative to those in the spectra of the starting material. Efforts are currently under way to understand the full role of the Lewis acid in these cooperative carbene catalytic processes.
  • 65
    • 79851498153 scopus 로고    scopus 로고
    • IV complexes does not provide the desired cyclopentane products. Further investigations in this area are ongoing
    • IV complexes does not provide the desired cyclopentane products. Further investigations in this area are ongoing.
  • 66
    • 77957925624 scopus 로고    scopus 로고
    • For a recent computational study that supports a conjugate-addition pathway over a benzoin/oxy-Cope process, see
    • For a recent computational study that supports a conjugate-addition pathway over a benzoin/oxy-Cope process, see:, L. R. Domingo, R. J. Zaragozá, M. Arnó, Org. Biomol. Chem. 2010, 8, 4884.
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 4884
    • Domingo, L.R.1    Zaragozá, R.J.2    Arnó, M.3
  • 67
    • 79851498966 scopus 로고    scopus 로고
    • 1Ha NMR spectroscopy (500a MHz). The mixed ester can be isolated by flash chromatography
    • 1Ha NMR spectroscopy (500a MHz). The mixed ester can be isolated by flash chromatography.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.