메뉴 건너뛰기




Volumn 17, Issue 3, 2011, Pages 984-992

Synthesis of chiral cyclic nitrones by asymmetric addition of β-ketosulfones to nitroalkenes followed by reductive cyclization

Author keywords

asymmetric synthesis; ketosulfones; Michael addition; nitrones; organocatalysis

Indexed keywords

ASYMMETRIC SYNTHESIS; KETOSULFONES; MICHAEL ADDITION; NITRONES; ORGANOCATALYSIS;

EID: 78651423073     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001914     Document Type: Article
Times cited : (46)

References (76)
  • 1
    • 11144263200 scopus 로고    scopus 로고
    • For recent reviews on organocatalysis, see P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286
    • (2004) Angew. Chem. , vol.116 , pp. 5248-5286
    • Dalko, P.I.1    Moisan, L.2
  • 2
  • 4
    • 33947198541 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1570-1581
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 1570-1581
  • 6
    • 78651422627 scopus 로고    scopus 로고
    • special edition No. 12, Chem. Rev. 2007, 107
    • (2007) Chem. Rev. , Issue.12 , pp. 107
  • 7
    • 34250757123 scopus 로고    scopus 로고
    • special issue on organocatalysis
    • special issue on organocatalysis:, Chimia 2007, 61, 212-281
    • (2007) Chimia , vol.61 , pp. 212-281
  • 11
    • 53549121402 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6138-6171
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6138-6171
  • 13
  • 15
    • 0002384398 scopus 로고
    • (tin enolates in Michael reaction)
    • T. Mukaiyama, S. Kobayashi, Org. React. 1994, 46, 1-103 (tin enolates in Michael reaction)
    • (1994) Org. React. , vol.46 , pp. 1-103
    • Mukaiyama, T.1    Kobayashi, S.2
  • 17
    • 0033936085 scopus 로고    scopus 로고
    • (enantioselective Michael reaction)
    • J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335 (enantioselective Michael reaction)
    • (2000) Acc. Chem. Res. , vol.33 , pp. 325-335
    • Johnson, J.S.1    Evans, D.A.2
  • 18
    • 0034986283 scopus 로고    scopus 로고
    • (vinylogous Michael reaction)
    • J. Christoffers, Synlett 2001, 723-732 (vinylogous Michael reaction)
    • (2001) Synlett , pp. 723-732
    • Christoffers, J.1
  • 21
    • 34250613134 scopus 로고    scopus 로고
    • For selected reviews on conjugated addition reactions using iminium-ion activation, see, for example S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716
    • (2007) Eur. J. Org. Chem. , pp. 1701-1716
    • Tsogoeva, S.B.1
  • 27
    • 8144225713 scopus 로고    scopus 로고
    • For selected reviews on thiourea catalysis, see
    • N. M. R. Hoffmann, J. Frakenpoh, Eur. J. Org. Chem. 2004, 4293-4312. For selected reviews on thiourea catalysis, see
    • (2004) Eur. J. Org. Chem. , pp. 4293-4312
    • Hoffmann, N.M.R.1    Frakenpoh, J.2
  • 30
    • 0142072631 scopus 로고    scopus 로고
    • For selected examples on conjugated addition reactions to nitroalkenes with bifunctional thiourea catalysts, see T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12672-12673
    • Okino, T.1    Hoashi, Y.2    Takemoto, Y.3
  • 36
    • 0002108906 scopus 로고
    • (Ed.: A. Padwa), Wiley, New York
    • For reviews on nitrones and related compounds, see J. J. Tufariello, in 1,3-Dipolar Cycloaddition Chemistry, Vol.2 (Ed.:, A. Padwa,), Wiley, New York, 1984, pp. 83-168
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.2 , pp. 83-168
    • Tufariello, J.J.1
  • 42
    • 18744403152 scopus 로고    scopus 로고
    • (Ed.: A. Padwa), Thieme, Stuttgart
    • P. Merino, in Science of Synthesis, Vol.27 (Ed.:, A. Padwa,), Thieme, Stuttgart, 2004, pp. 511-580
    • (2004) Science of Synthesis , vol.27 , pp. 511-580
    • Merino, P.1
  • 44
    • 29144485901 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 7832-7835
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 7832-7835
  • 51
    • 77950477105 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 2668-2679
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2668-2679
  • 58
    • 33746290813 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 4305-4309
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 4305-4309
  • 62
    • 77953955584 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 4656-4660
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 4656-4660
  • 65
    • 78651430952 scopus 로고    scopus 로고
    • note
    • The significantly higher enantiomeric ratios obtained with compounds 3 / 5a and 3 / 5f and in large-scale reactions might suggest an enrichment of the enantiomeric ratio by partial crystallization of these products; however, several experiments in two different laboratories and the use of polar solvents to avoid unintentional crystallization by manipulation of the samples ruled out this possibility; nonlinear effects and other experimental issues could affect the enantioselectivity.
  • 67
    • 78651467448 scopus 로고    scopus 로고
    • note
    • 3).
  • 68
    • 0001491269 scopus 로고
    • For related simultaneous reduction/cyclization of oxonitro derivatives to nitrones, see.
    • For related simultaneous reduction/cyclization of oxonitro derivatives to nitrones, see:, D. L. Haire, J. W. Hilborn, E. G. Janzen, J. Org. Chem. 1986, 51, 4298-4300.
    • (1986) J. Org. Chem. , vol.51 , pp. 4298-4300
    • Haire, D.L.1    Hilborn, J.W.2    Janzen, E.G.3
  • 70
    • 78651443508 scopus 로고    scopus 로고
    • note
    • The yield of nitrone 5a was increased to 80% by shortening the reaction time to 5-10min and using freshly activated Zn.
  • 71
    • 78651429795 scopus 로고    scopus 로고
    • note
    • CCDC-777231 (rac-5 a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
  • 74
    • 78651422626 scopus 로고    scopus 로고
    • CCDC-777232 ((2R,3S,4R)- 6 e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via. The data set was collected with a Nonius KappaCCD diffractometer; programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol, 1997, 276, 307-326), absorption correction Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. 2003, A59, 228-234), structure solution SHELXS-97 (G.M. Sheldrick, Acta Crystallogr. Sect. A. 1990, 46, 467-473), structure refinement SHELXL-97 (G.M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122), graphics SCHAKAL (E. Keller, Univ. Freiburg, 1997).
    • CCDC-777232 ((2R,3S,4R)- 6 e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via. The data set was collected with a Nonius KappaCCD diffractometer; programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol, 1997, 276, 307-326), absorption correction Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. 2003, A59, 228-234), structure solution SHELXS-97 (G.M. Sheldrick, Acta Crystallogr. Sect. A. 1990, 46, 467-473), structure refinement SHELXL-97 (G.M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122), graphics SCHAKAL (E. Keller, Univ. Freiburg, 1997).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.