메뉴 건너뛰기




Volumn 52, Issue 20, 2013, Pages 5360-5363

Control of remote stereochemistry in the synthesis of spirocyclic oxindoles: Vinylogous organocascade catalysis

Author keywords

aldol reaction; organocatalysis; spirocompounds; synthetic methods; vinylogous reactivity

Indexed keywords

ALDOL REACTIONS; ORGANOCATALYSIS; SPIRO-COMPOUNDS; SYNTHETIC METHODS; VINYLOGOUS REACTIVITIES;

EID: 84877260441     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201301017     Document Type: Article
Times cited : (115)

References (55)
  • 2
    • 33750977591 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7134-7186
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7134-7186
  • 5
    • 33947198541 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1570-1581
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 1570-1581
  • 13
    • 0009297190 scopus 로고
    • R. C. Fuson, Chem. Rev. 1935, 16, 1-27. For an overview of vinylogous reactivity in aminocatalysis, see
    • (1935) Chem. Rev. , vol.16 , pp. 1-27
    • Fuson, R.C.1
  • 15
    • 84861510484 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 5290-5292.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 5290-5292
  • 18
    • 84866492507 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 9748-9770
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 9748-9770
  • 23
    • 61349093028 scopus 로고    scopus 로고
    • For a review highlighting the difficulties of controlling remote stereocenters, see:, J. Clayden, Chem. Soc. Rev. 2009, 38, 817-829.
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 817-829
    • Clayden, J.1
  • 26
    • 78650090073 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 9685-9688
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 9685-9688
  • 30
    • 84862679331 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 6439-6442.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 6439-6442
  • 31
    • 84865845003 scopus 로고    scopus 로고
    • We note that 3-substituted alkyl/aryl oxindoles, which lack the electrophilic carbonyl moiety needed for a cascade reaction to happen, remained completely inert toward the 1,6-addition to dienone 1 a under the catalysis of A. In addition, by-products arising from a discrete 1,6-addition manifold of 2 (i.e., failure of the dienamine-driven cyclization step) have never been detected in this study. For an example of organocatalytic tandem reaction where the second step provides the thermodynamic driving force for the cascade to proceed to completion, see:, G. Talavera, E. Reyes, J. L. Vicario, L. Carrillo, Angew. Chem. 2012, 124, 4180-4183
    • (2012) Angew. Chem. , vol.124 , pp. 4180-4183
    • Talavera, G.1    Reyes, E.2    Vicario, J.L.3    Carrillo, L.4
  • 32
    • 84859968475 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 4104-4107.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4104-4107
  • 34
    • 84859560876 scopus 로고    scopus 로고
    • K. Albertshofer, B. Tan, C. F. Barbas III, Org. Lett. 2012, 14, 1834-1837. During the preparation of this manuscript, a report was published in which 2 served to realize a traditional iminium ion-enamine cascade with α,β-unsaturated aldehydes, see
    • (2012) Org. Lett. , vol.14 , pp. 1834-1837
    • Albertshofer, K.1    Tan, B.2    Barbas III, C.F.3
  • 41
    • 70349784950 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 7200-7203
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7200-7203
  • 43
    • 84855993419 scopus 로고    scopus 로고
    • See also Refs. [12]
    • Angew. Chem. Int. Ed. 2012, 51, 971-974. See also Refs. [12].
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 971-974
  • 45
    • 36749025633 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8748-8758
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8748-8758
  • 47
    • 70349784870 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 3224-3242
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 3224-3242
  • 49
    • 77956280420 scopus 로고    scopus 로고
    • M. Rottmann, et al., Science 2010, 329, 1175-1180.
    • (2010) Science , vol.329 , pp. 1175-1180
    • Rottmann, M.1
  • 50
    • 84874100756 scopus 로고    scopus 로고
    • We recently found that the catalyst E can infer a high enantiocontrol in dienamine-based reactions of cyclic enones:, D. Bastida, Y. Liu, X. Tian, E. Escudero-Adán, P. Melchiorre, Org. Lett. 2013, 15, 220-223. However, this bifunctional catalyst performs poorly in the present cascade reaction.
    • (2013) Org. Lett. , vol.15 , pp. 220-223
    • Bastida, D.1    Liu, Y.2    Tian, X.3    Escudero-Adán, E.4    Melchiorre, P.5
  • 51
    • 84877305758 scopus 로고    scopus 로고
    • CCDC 918015 (3 d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 918015 (3 d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 54
    • 79956067261 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 5095-5098
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5095-5098


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.