메뉴 건너뛰기




Volumn , Issue 13, 2007, Pages 2100-2106

Efficient one-pot synthesis of enantiomerically pure 2-(hydroxymethyl)- morpholines

Author keywords

Asymmetric synthesis; Cyclization; Epichlorohydrin; Morpholines; Nitrogen heterocycles

Indexed keywords


EID: 34250315080     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601006     Document Type: Article
Times cited : (46)

References (43)
  • 4
    • 0032425787 scopus 로고    scopus 로고
    • 2: a J. Ong, D. I. B. Kerr, H. Bittiger, P. C. Waldmeier, P. A. Baumann, N. G. Cooke, S. J. Mickel, W. Froestl, Eur. J. Pharmacol. 1998, 362, 27-34;
    • 2: a) J. Ong, D. I. B. Kerr, H. Bittiger, P. C. Waldmeier, P. A. Baumann, N. G. Cooke, S. J. Mickel, W. Froestl, Eur. J. Pharmacol. 1998, 362, 27-34;
  • 5
    • 34250624134 scopus 로고    scopus 로고
    • 3: b S. Kawashima, T. Matsuno, S. Yaguchi, H. Sasahara, T. Watanabe, T. PCT Int. Appl. WO 02088112, 2002;
    • 3: b) S. Kawashima, T. Matsuno, S. Yaguchi, H. Sasahara, T. Watanabe, T. PCT Int. Appl. WO 02088112, 2002;
  • 6
    • 34250631417 scopus 로고    scopus 로고
    • 4: c R. A. Ancliff, C. M. Cook, C. D. Eldred, P. M. Gore, L. A. Harrison, M. A. Hayes, S. T. Hodgson, D. B. Judd, S. E. Keeling, X. Q. Lewell, G. Mills, G. M. Robertson, S. Swanson, A. J. Walker, M. Wilkinson, PCT Int. Appl. WO 03082861, 2003;
    • 4: c) R. A. Ancliff, C. M. Cook, C. D. Eldred, P. M. Gore, L. A. Harrison, M. A. Hayes, S. T. Hodgson, D. B. Judd, S. E. Keeling, X. Q. Lewell, G. Mills, G. M. Robertson, S. Swanson, A. J. Walker, M. Wilkinson, PCT Int. Appl. WO 03082861, 2003;
  • 7
    • 0026073882 scopus 로고    scopus 로고
    • 5: d S. Kato, T. Morie, T. Kon, N. Yoshida, T. Karasawa, J. Matsumoto, J. Med. Chem. 1991, 34, 616-624.
    • 5: d) S. Kato, T. Morie, T. Kon, N. Yoshida, T. Karasawa, J. Matsumoto, J. Med. Chem. 1991, 34, 616-624.
  • 8
    • 34250625754 scopus 로고    scopus 로고
    • For modifications of the 2-(hydroxymethyl) group in morpholines of type 6, see refs.[5a,5b,9,11a
    • [5a,5b,9,11a]
  • 13
    • 8444232793 scopus 로고    scopus 로고
    • For non-stereoselective syntheses of 2-substituted morpholines see: a
    • For non-stereoselective syntheses of 2-substituted morpholines see: a) V. Lupi, D. Albanese, D. Landini, D. Scaletti, M. Penso, Tetrahedron 2004, 60, 11709-11718;
    • (2004) Tetrahedron , vol.60 , pp. 11709-11718
    • Lupi, V.1    Albanese, D.2    Landini, D.3    Scaletti, D.4    Penso, M.5
  • 18
    • 34250681876 scopus 로고    scopus 로고
    • Ref.[5b
    • [5b]
  • 19
    • 1642486447 scopus 로고    scopus 로고
    • For a related procedure leading to 2-(siloxyalkyl)-substituted morpholines, see
    • b) For a related procedure leading to 2-(siloxyalkyl)-substituted morpholines, see: B. A. Lanman, A. G. Myers, Org. Lett. 2004, 6, 1045-1047.
    • (2004) Org. Lett , vol.6 , pp. 1045-1047
    • Lanman, B.A.1    Myers, A.G.2
  • 22
    • 20444362011 scopus 로고    scopus 로고
    • M. C. Wilkinson, Tetrahedron Lett. 2005, 46, 4773-4775 and references cited therein;
    • a) M. C. Wilkinson, Tetrahedron Lett. 2005, 46, 4773-4775 and references cited therein;
  • 24
    • 33751333267 scopus 로고    scopus 로고
    • For a review on the asymmetric ring opening of epoxides with carbon nucleophiles, see
    • For a review on the asymmetric ring opening of epoxides with carbon nucleophiles, see: M. Pineschi, Eur. J. Org. Chem. 2006, 4979-4988.
    • (2006) Eur. J. Org. Chem , pp. 4979-4988
    • Pineschi, M.1
  • 27
    • 34250614782 scopus 로고    scopus 로고
    • J. Chem. Res. (M) 1999, 3, 1001-1047;
    • (1999) , Issue.3 , pp. 1001-1047
    • Chem, J.1    Res, M.2
  • 29
    • 34250666737 scopus 로고    scopus 로고
    • ref.[5a
    • [5a]
  • 32
    • 34250668472 scopus 로고    scopus 로고
    • This was necessary in order to exclude the formation of oxazepanes 11 or epoxides 10 see Scheme 2 and Table 2, which possess identical masses and would provide similar 1H and 13C NMR spectra
    • 13C NMR spectra.
  • 33
    • 0022356177 scopus 로고    scopus 로고
    • For the debenzylation of 6a, see: a T. Kojima, K. Niigata, T. Fujikura, S. Tachikawa, Y. Nozaki, S. Kagami, K. Takahashi, Chem. Pharm. Bull. 1985, 33, 3766-3774;
    • For the debenzylation of 6a, see: a) T. Kojima, K. Niigata, T. Fujikura, S. Tachikawa, Y. Nozaki, S. Kagami, K. Takahashi, Chem. Pharm. Bull. 1985, 33, 3766-3774;
  • 35
    • 34250687181 scopus 로고    scopus 로고
    • ref.[14b
    • [14b]
  • 36
    • 34250685856 scopus 로고    scopus 로고
    • 1H NMR spectra of the crude reaction mixtures. Nevertheless, the formation of small amounts of diastereomeric byproducts cannot be excluded.
    • 1H NMR spectra of the crude reaction mixtures. Nevertheless, the formation of small amounts of diastereomeric byproducts cannot be excluded.
  • 43
    • 34250663158 scopus 로고    scopus 로고
    • [5d,14a,14b]
    • [5d,14a,14b]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.