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Volumn 9, Issue 23, 2007, Pages 4841-4844

Exploring modular domino reactions: Competing processes based on the nature of the angular substituent

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND;

EID: 36348961994     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7021643     Document Type: Article
Times cited : (9)

References (26)
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    • Shibasaki, M, Stoddart, J. F, Vogtle, F, Eds, Wiley-VCH: Weinheim, Germany
    • (d) Tietze, L. F.; Haunert, F. In Stimulating Concepts in Chemistry; Shibasaki, M., Stoddart, J. F., Vogtle, F., Eds.; Wiley-VCH: Weinheim, Germany, 2000; pp 39-64.
    • (2000) Stimulating Concepts in Chemistry , pp. 39-64
    • Tietze, L.F.1    Haunert, F.2
  • 5
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    • Tietze, L. F, Brasche, G, Gericke, K. M, Eds, Wiley-VCH: Weinheim, Germany, ISBN: 3-527-29060-5
    • (e) Domino Reactions In Organic Synthesis; Tietze, L. F., Brasche, G., Gericke, K. M., Eds.; Wiley-VCH: Weinheim, Germany, 2006; ISBN: 3-527-29060-5.
    • (2006) Domino Reactions In Organic Synthesis
  • 6
    • 0041864168 scopus 로고    scopus 로고
    • The probe used is an unsaturated bicyclic 1,2-diol having a variable substitution pattern. Advantages are the very rapid increase in molecular complexity and its modular character. (a) Finet, L.; Candela Lena, J. I.; Kaoudi, T.; Birlirakis, N.; Arseniyadis, S. Chem. - Eur. J. 2003, 9, 3813-3820.
    • The probe used is an unsaturated bicyclic 1,2-diol having a variable substitution pattern. Advantages are the very rapid increase in molecular complexity and its modular character. (a) Finet, L.; Candela Lena, J. I.; Kaoudi, T.; Birlirakis, N.; Arseniyadis, S. Chem. - Eur. J. 2003, 9, 3813-3820.
  • 11
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    • 4: Criegee, R.; Beucker, H. Ann. Chem. 1939, 541, 218-238.
    • 4: Criegee, R.; Beucker, H. Ann. Chem. 1939, 541, 218-238.
  • 12
    • 85033148217 scopus 로고    scopus 로고
    • 2+ but without the toxic and environmental issues: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447.
    • 2+ but without the toxic and environmental issues: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447.
  • 20
    • 0002549529 scopus 로고
    • For a discussion of pericyclic reaction transition states, see
    • For a discussion of pericyclic reaction transition states, see: Houk, K. N.; Gonzales, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81-90.
    • (1995) Acc. Chem. Res , vol.28 , pp. 81-90
    • Houk, K.N.1    Gonzales, J.2    Li, Y.3
  • 21
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    • Best preparation of the common intermediate 1: (a) Jung, M. E.; Piizzi, G. Org. Lett. 2003, 5, 137-140.
    • Best preparation of the common intermediate 1: (a) Jung, M. E.; Piizzi, G. Org. Lett. 2003, 5, 137-140.
  • 23
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    • It should be pointed out that all domino reactions are performed on crude diastereomeric mixtures; we only show the stereopure target diols for characterization purposes, by separating various amounts of stereopure compounds using the eluent indicated in the experimental part
    • It should be pointed out that all domino reactions are performed on crude diastereomeric mixtures; we only show the stereopure target diols for characterization purposes, by separating various amounts of stereopure compounds using the eluent indicated in the experimental part.
  • 25
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    • 3.
    • 3.
  • 26
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    • 13C NMR of the crude material showed no resonances other than those due to the expected products 16-21.
    • 13C NMR of the crude material showed no resonances other than those due to the expected products 16-21.


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