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Volumn , Issue 12, 2005, Pages 2449-2458

Sequential diastereoselective addition of allylic and homoallylic grignard reagents to 2-Acyl-perhydro-1,3-benzoxazines and ring-closing Metathesis: An asymmetric route to azepin-3-ol and azocin-3-ol derivatives

Author keywords

Amino alcohols; Asymmetric synthesis; Azaheterocycles; Ring closing metathesis

Indexed keywords


EID: 20744434418     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400836     Document Type: Article
Times cited : (21)

References (60)
  • 1
    • 0026093828 scopus 로고
    • For a review of medium ring nitrogen heterocycles, see: P. A. Evans, A. B. Holmes, Tetrahedron 1991, 47, 9131.
    • (1991) Tetrahedron , vol.47 , pp. 9131
    • Evans, P.A.1    Holmes, A.B.2
  • 3
    • 2942557280 scopus 로고    scopus 로고
    • For a recent review of transition metal-catalyzed reactions in heterocyclic synthesis, see: I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127.
    • (2004) Chem. Rev. , vol.104 , pp. 2127
    • Nakamura, I.1    Yamamoto, Y.2
  • 4
    • 0034246704 scopus 로고    scopus 로고
    • For a review on metal-mediated synthesis of medium-size rings, see: L. Yet, Chem. Rev. 2000, 100, 2963.
    • (2000) Chem. Rev. , vol.100 , pp. 2963
    • Yet, L.1
  • 15
    • 0001811974 scopus 로고    scopus 로고
    • For reviews in synthesis of nitrogen-containing cyclic compounds by RCM, see: a) A. J. Phillips, A. D. Abell, Aldrichimica Acta 1999, 32, 75;
    • (1999) Aldrichimica Acta , vol.32 , pp. 75
    • Phillips, A.J.1    Abell, A.D.2
  • 19
    • 0034674322 scopus 로고    scopus 로고
    • For a review of the synthesis of medium-size rings by the RCM reaction, see: M. E. Maier, Angew. Chem. Int. Ed. 2000, 39, 2073.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2073
    • Maier, M.E.1
  • 35
    • 78249281266 scopus 로고
    • Despite the fact that the Grubbs' ruthenium carbene complexes show remarkable functional group tolerance, the tolerance is generally poor for amines: a) G. C. Fu, S.-B. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1993, 115, 9856;
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9856
    • Fu, G.C.1    Nguyen, S.-B.T.2    Grubbs, R.H.3
  • 38
    • 0033518577 scopus 로고    scopus 로고
    • For some examples of ring-closing metathesis of substrates containing unprotected tertiary amino functionalities in the presence of a ruthenium complex see: a) S. F. Martin, J. H. Humphrey, A. Ali, M. C. Hillier, J. Am. Chem. Soc. 1999, 121, 866;
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 866
    • Martin, S.F.1    Humphrey, J.H.2    Ali, A.3    Hillier, M.C.4
  • 42
    • 0038163433 scopus 로고    scopus 로고
    • This strategy has been successfully used to avoid the formation of chelates between the ruthenium carbene and other polar groups, a) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130;
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9130
    • Fürstner, A.1    Langemann, K.2
  • 43
    • 0033063994 scopus 로고    scopus 로고
    • See also Ref. 6e and references cited therein
    • b) P. Wipf, W. S. Weiner, J. Org. Chem. 1999, 64, 5321. See also Ref. 6e and references cited therein.
    • (1999) J. Org. Chem. , vol.64 , pp. 5321
    • Wipf, P.1    Weiner, W.S.2
  • 45
    • 0034729582 scopus 로고    scopus 로고
    • It has been demonstrated that ammonium salts are tolerated by the Grubbs' ruthenium catalyst: a) D. L. Wright, J. P. Schulte, II, M. A. Page, Org. Lett. 2000, 2, 1847;
    • (2000) Org. Lett. , vol.2 , pp. 1847
    • Wright, D.L.1    Schulte II, J.P.2    Page, M.A.3
  • 50
    • 0037162784 scopus 로고    scopus 로고
    • and references cited therein
    • Only in particular cases have seven-membered rings with tri-substituted double bonds been successfully formed by RCM: K. Nakashima, K. Inoue, M. Sono, M. Tori, J. Org. Chem. 2002, 67, 6034 and references cited therein.
    • (2002) J. Org. Chem. , vol.67 , pp. 6034
    • Nakashima, K.1    Inoue, K.2    Sono, M.3    Tori, M.4
  • 52
  • 54
    • 0001101871 scopus 로고    scopus 로고
    • Differences in the rates of formation of isomeric cycloheptenes have been reported elsewhere: a) T. A. Kirkland, R. H. Grubbs, J. Org. Chem. 1997, 62, 7310;
    • (1997) J. Org. Chem. , vol.62 , pp. 7310
    • Kirkland, T.A.1    Grubbs, R.H.2
  • 57
    • 20744453482 scopus 로고    scopus 로고
    • CCDC-260740 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.
  • 59
    • 20744456565 scopus 로고    scopus 로고
    • note
    • For the preparation of benzoxazine 7f commercially available (Aldrich) 2-methylallylmagnesium chloride was used.
  • 60
    • 20744448492 scopus 로고    scopus 로고
    • note
    • The hydrochlorides of 7a-i were obtained by bubbling dry HCl into ethereal solutions of 7a-i for 5 min and removal of the solvent.


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