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Volumn 71, Issue 10, 2006, Pages 3923-3927

Mix-and-heat benzylation of alcohols using a bench-stable pyridinium salt

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; HEATING; NITROGEN COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33646520636     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0602773     Document Type: Article
Times cited : (114)

References (35)
  • 3
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    • Gawley, R. E.; Aubé, J. In Principles of Asymmetric Synthesis; Baldwin, J. E., Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series 14; Pergamon: Tarrytown, NY, 1996; pp 121-134.
    • (1996) Principles of Asymmetric Synthesis , pp. 121-134
    • Gawley, R.E.1    Aubé, J.2
  • 4
    • 0004288915 scopus 로고    scopus 로고
    • Hanessian, S., Ed.; Marcel Dekker: New York
    • (a) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997.
    • (1997) Preparative Carbohydrate Chemistry
  • 7
    • 0033597612 scopus 로고    scopus 로고
    • Recent arylmethyl protecting groups that are cleaved under mild conditions: (a) Jobron, L.; Hindsgaul, O. J. Am. Chem. Soc. 1999, 121, 5835-5836.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5835-5836
    • Jobron, L.1    Hindsgaul, O.2
  • 13
    • 33646535889 scopus 로고
    • Benzyl 2,2,2-trichloroacetimidate
    • Paquette, L. A., Ed.; John Wiley and Sons: New York
    • Boa, A. N.; Jenkins, P. R. Benzyl 2,2,2-Trichloroacetimidate. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley and Sons: New York, 1995; Vol. 1, pp 374-375.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.1 , pp. 374-375
    • Boa, A.N.1    Jenkins, P.R.2
  • 14
    • 33646534452 scopus 로고    scopus 로고
    • note
    • p-Methoxybenzyl (PMB) ethers may be formed under mild conditions that do not extend to benzylation (ref 1).
  • 18
    • 0343643766 scopus 로고
    • 2-Chloro-1-methylpyridinium iodide
    • Paquette, L. A., Ed.; John Wiley and Sons: New York
    • (a) Armstrong, A. 2-Chloro-1-methylpyridinium Iodide. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley and Sons: New York, 1995; Vol. 2, pp 1174-1175.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.2 , pp. 1174-1175
    • Armstrong, A.1
  • 26
    • 33646521096 scopus 로고    scopus 로고
    • note
    • Recrystallization of 1 from THF has no discernible effect on its properties.
  • 28
    • 0002974335 scopus 로고
    • 1H NMR spectra of the crude product mixtures after aqueous workup. (Diagram presented)
    • (1990) Org. React. , vol.38 , pp. 1
    • Ager, D.J.1
  • 29
    • 33646523658 scopus 로고    scopus 로고
    • note
    • 3N (2.0 equiv), and TBSC1 (1.1 equiv). See the Supporting Information for characterization data.
  • 30
    • 33646530551 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra because the diagnostic benzylic singlets were coincident.
  • 32
    • 33646503748 scopus 로고    scopus 로고
    • note
    • Methoxypyridinium triflate 10 was prepared in 85% yield (unoptimized) by a procedure similar to that used for the preparation of 1. See the Supporting Information for characterization data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.