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Volumn 51, Issue 20, 2010, Pages 2708-2712

Organocatalytic diastereoselective dibromination of alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CINNAMALDEHYDE; PYRROLIDINE DERIVATIVE; SUCCINIMIDE;

EID: 77950627874     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.043     Document Type: Article
Times cited : (26)

References (37)
  • 5
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    • Budavari S., O'Neil M.J., Smith A., Heckelman P.E., and Kinneary J.F. (Eds), Merck, Rahway
    • In: Budavari S., O'Neil M.J., Smith A., Heckelman P.E., and Kinneary J.F. (Eds). The Merck Index. 12th ed. (1996), Merck, Rahway
    • (1996) The Merck Index. 12th ed.
  • 6
    • 2942729965 scopus 로고    scopus 로고
    • and references cited therein
    • Salazar J., and Dorta R. Synlett (2004) 1318 and references cited therein
    • (2004) Synlett , pp. 1318
    • Salazar, J.1    Dorta, R.2
  • 11
    • 33947198541 scopus 로고    scopus 로고
    • For an excellent review on organocatalytic domino reactions, see:
    • For an excellent review on organocatalytic domino reactions, see:. Enders D., Grondal C., and Hüttl M.R.M. Angew. Chem., Int. Ed. 46 (2007) 1570
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 1570
    • Enders, D.1    Grondal, C.2    Hüttl, M.R.M.3
  • 12
    • 2342614099 scopus 로고    scopus 로고
    • For selected examples of organocatalytic asymmetric domino and cascade reactions, see:
    • For selected examples of organocatalytic asymmetric domino and cascade reactions, see:. Halland N., Aburell P.S., and Jørgensen K.A. Angew. Chem., Int. Ed. 43 (2004) 1272
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1272
    • Halland, N.1    Aburell, P.S.2    Jørgensen, K.A.3
  • 33
    • 77950630045 scopus 로고    scopus 로고
    • note
    • R2 = 45.1 min.
  • 34
    • 77950626563 scopus 로고    scopus 로고
    • 3 (1 mL) were successively added NBS (1.1 mmol, recrystallized from boiling water), succinimide (0.1 mmol) and pyrrolidine (0.1 mmol). The reaction vial was sealed and the mixture was stirred at 60 °C for the time indicated in Table 3. After the reaction was complete, the corresponding dibromo product 3 was separated by flash chromatography on silica gel. The spectral data were in accordance with the literature: compound 3j: (a) Dewkar, G. K.; Narina, S. V.; Sudalai, A. Org. Lett. 2003, 5, 4501-4504. Compound 3i: (b) Lexa, D.; Saveant, J. M.; Schaefer, H. J.; Binh, S. K.; Vering, B.; Wang, D.-L. J. Am. Chem. Soc. 1990, 112, 6162-6177. Compounds 3k, 3l and 3m: (c) Butcher, T. S.; Zhou, F.; Detty, M. R. J. Org. Chem. 1998, 63, 169-176; (d) Ye, C.-F.; Shreeve, J. M. J. Org. Chem. 2004, 69, 8561-8563.
    • 3 (1 mL) were successively added NBS (1.1 mmol, recrystallized from boiling water), succinimide (0.1 mmol) and pyrrolidine (0.1 mmol). The reaction vial was sealed and the mixture was stirred at 60 °C for the time indicated in Table 3. After the reaction was complete, the corresponding dibromo product 3 was separated by flash chromatography on silica gel. The spectral data were in accordance with the literature: compound 3j: (a) Dewkar, G. K.; Narina, S. V.; Sudalai, A. Org. Lett. 2003, 5, 4501-4504. Compound 3i: (b) Lexa, D.; Saveant, J. M.; Schaefer, H. J.; Binh, S. K.; Vering, B.; Wang, D.-L. J. Am. Chem. Soc. 1990, 112, 6162-6177. Compounds 3k, 3l and 3m: (c) Butcher, T. S.; Zhou, F.; Detty, M. R. J. Org. Chem. 1998, 63, 169-176; (d) Ye, C.-F.; Shreeve, J. M. J. Org. Chem. 2004, 69, 8561-8563. Compound 3m': (e) Donohoe, T. J.; Fishlock, L. P.; Procopiou, P. A. Org. Lett. 2008, 10, 285-288.
  • 35
    • 77950629083 scopus 로고    scopus 로고
    • note
    • CCDC 745659 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.