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Volumn 9, Issue 26, 2007, Pages 5441-5444

Lewis acid-mediated unprecedented ring-opening rearrangement of 2-Aryl-N-tosylazetidines to enantiopure (E)-allylamines

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EID: 38349165658     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7023218     Document Type: Article
Times cited : (52)

References (50)
  • 1
    • 84943375045 scopus 로고
    • Lwowski, W, Ed, Pergamon: Oxford, UK
    • (a) Davies, D. E.; Storr, R. C. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, UK, 1984; Vol. 7, Part 5, pp 237-284.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.7 , Issue.PART 5 , pp. 237-284
    • Davies, D.E.1    Storr, R.C.2
  • 24
    • 33745222531 scopus 로고    scopus 로고
    • N2-type ring-opening of N-tosylazetidines: (a) Ghorai, M. K.; Das, K.; Kumar, A.; Das, A. Tetrahedron Lett. 2006, 47, 5393.
    • N2-type ring-opening of N-tosylazetidines: (a) Ghorai, M. K.; Das, K.; Kumar, A.; Das, A. Tetrahedron Lett. 2006, 47, 5393.
  • 27
    • 18844399915 scopus 로고    scopus 로고
    • N2- type ring-opening of N-tosylaziridines; (a) Ghorai, M. K.; Das, K.; Kumar. A.; Ghosh, K. Tetrahedron Lett. 2005, 46, 4103.
    • N2- type ring-opening of N-tosylaziridines; (a) Ghorai, M. K.; Das, K.; Kumar. A.; Ghosh, K. Tetrahedron Lett. 2005, 46, 4103.
  • 47
    • 38349192710 scopus 로고    scopus 로고
    • A similar mechanism operates in other coordinating solvents THF, DMF
    • A similar mechanism operates in other coordinating solvents (THF, DMF).
  • 48
    • 38349101789 scopus 로고    scopus 로고
    • We proposed a similar type of six-membered transition state for oxidative cleavage of 2-phenyl-N-tosylaziridine by DMSO to α-amino ketone as the only product (Ghorai, M. K. Unpublished result). Figure presented.
    • (a) We proposed a similar type of six-membered transition state for oxidative cleavage of 2-phenyl-N-tosylaziridine by DMSO to α-amino ketone as the only product (Ghorai, M. K. Unpublished result). Figure presented.
  • 49
    • 33646518818 scopus 로고    scopus 로고
    • A similar oxidative ring-opening of aziridine-1-carboxylates to α-amino ketones by DMSO was reported earlier, see: Fujita, S.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1969, 21, 1677.
    • (b) A similar oxidative ring-opening of aziridine-1-carboxylates to α-amino ketones by DMSO was reported earlier, see: Fujita, S.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1969, 21, 1677.
  • 50
    • 38349174936 scopus 로고    scopus 로고
    • The synthesis of azetidines 43 and 46 is described in the Supporting Information (pp S-12).
    • The synthesis of azetidines 43 and 46 is described in the Supporting Information (pp S-12).


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