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Volumn , Issue 14, 2006, Pages 3259-3265

An efficient and diastereoselective intramolecular 1,3-dipolar cycloaddition of cyclic azomethine ylides and nitrones

Author keywords

Asymmetric synthesis; Cyclizations; Dipolar cycloaddition; Isoxazolidines; Pyrrolidines

Indexed keywords


EID: 33746066351     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600242     Document Type: Article
Times cited : (14)

References (74)
  • 1
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    • I. W. Southon, J. Buckingham (Eds.), Chapman & Hall, New York
    • I. W. Southon, J. Buckingham (Eds.), Dictionary of Alkaloids, Chapman & Hall, New York, 1989.
    • (1989) Dictionary of Alkaloids
  • 7
    • 0031012571 scopus 로고    scopus 로고
    • For some reviews on nitrones, see: a) M. Frederickson, Tetrahedron 1997, 53, 403;
    • (1997) Tetrahedron , vol.53 , pp. 403
    • Frederickson, M.1
  • 14
    • 11544346529 scopus 로고    scopus 로고
    • For a review on asymmetric 1,3-dipolar cycloaddition reactions see: K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863.
    • (1998) Chem. Rev. , vol.98 , pp. 863
    • Gothelf, K.V.1    Jørgensen, K.A.2
  • 18
    • 0034699058 scopus 로고    scopus 로고
    • For a review on catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones, see: a) K. V. Gothelf, K. A. Jørgensen, Chem. Commun. 2000, 1449.
    • (2000) Chem. Commun. , pp. 1449
    • Gothelf, K.V.1    Jørgensen, K.A.2
  • 23
    • 10044231720 scopus 로고    scopus 로고
    • For illustrative examples using stoichiometric chiral auxiliaries attached on the azomethine ylide, see: a) K. A. Ahrendt, R. M. Williams, Org. Lett. 2004, 6, 4539;
    • (2004) Org. Lett. , vol.6 , pp. 4539
    • Ahrendt, K.A.1    Williams, R.M.2
  • 27
  • 36
    • 24944492138 scopus 로고    scopus 로고
    • For some examples on the use of stoichiometric chiral auxiliaries attached on the dipolarophile substrate in cycloadditions with nitrones: a) E. Tyrrell, J. Allen, K. Jones, R. Beauchet, Synthesis 2005, 2393;
    • (2005) Synthesis , pp. 2393
    • Tyrrell, E.1    Allen, J.2    Jones, K.3    Beauchet, R.4
  • 60
    • 0033548694 scopus 로고    scopus 로고
    • For examples of intramolecular 1,3-dipolar cycloadditions of azomethine ylides generated by the decarboxylative route, see: a) C. J. Lovely, H. Mahmud, Tetrahedron Lett. 1999, 40, 2079;
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2079
    • Lovely, C.J.1    Mahmud, H.2
  • 70
    • 0001187881 scopus 로고
    • Formation of the enamine tautomer rather than the azomethine ylide by condensation of an α-amino ester with an aldehyde containing an α-proton has been described previously: a) O. Tsuge, S. Kanemasa, M. Ohe, K. Yorozu, S. Takenaka, K. Ueno, Bull. Chem. Soc. Jpn. 1987, 60, 4067.
    • (1987) Bull. Chem. Soc. Jpn. , vol.60 , pp. 4067
    • Tsuge, O.1    Kanemasa, S.2    Ohe, M.3    Yorozu, K.4    Takenaka, S.5    Ueno, K.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.