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Volumn 74, Issue 6, 2009, Pages 2452-2459

Addition reactions of chloro- Or iodomethyllithium to imines. Synthesis of enantiopure aziridines and β-chloroamines

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINES; CHLOROALKANES; CHLOROAMINES; CHLOROIODOMETHANE; EFFICIENT SYNTHESIS; ENANTIOPURE; IN-SITU; METHYLLITHIUM;

EID: 64149085457     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802596y     Document Type: Article
Times cited : (47)

References (117)
  • 30
    • 64149115226 scopus 로고    scopus 로고
    • Reference 6b
    • (l) Reference 6b.
  • 32
    • 4544351364 scopus 로고    scopus 로고
    • Concellón, J. M.; Álvarez, J. R.; Garc?́a-Granda, S.; D?́az, M. R. Angew. Chem., Int. Ed. 2004, 43, 4333-4336.
    • (b) Concellón, J. M.; Álvarez, J. R.; Garc?́a-Granda, S.; D?́az, M. R. Angew. Chem., Int. Ed. 2004, 43, 4333-4336.
  • 43
    • 0030907093 scopus 로고    scopus 로고
    • To see recent reviews on the synthesis of aziridine: (a) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693-1715.
    • To see recent reviews on the synthesis of aziridine: (a) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693-1715.
  • 51
    • 0035917359 scopus 로고    scopus 로고
    • Concellón, J. M.; Bernad, P. L.; Riego, E.; Garc?́a-Granda, S.; Forcén-Acebal, A. J. Org. Chem. 2001, 66, 2764-2768.
    • (e) Concellón, J. M.; Bernad, P. L.; Riego, E.; Garc?́a-Granda, S.; Forcén-Acebal, A. J. Org. Chem. 2001, 66, 2764-2768.
  • 55
    • 0030561371 scopus 로고    scopus 로고
    • Garc?́a-Ruano, J. L.; Fernández, I.; del Pradoatalina, M.; Alcudia-Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414.
    • (a) Garc?́a-Ruano, J. L.; Fernández, I.; del Pradoatalina, M.; Alcudia-Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414.
  • 70
    • 64149089274 scopus 로고    scopus 로고
    • Reference 12b
    • (h) Reference 12b.
  • 72
    • 64149128502 scopus 로고    scopus 로고
    • For reviews on the synthesis and synthetic applications of functionalized halomethyllithium compounds: (a) Nájera, C, Yus, M. Trends Org. Chem. 1991, 2, 155-181
    • For reviews on the synthesis and synthetic applications of functionalized halomethyllithium compounds: (a) Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
  • 78
    • 0035935144 scopus 로고    scopus 로고
    • A synthesis of epoxides has been reported by reaction of iodomethyllithium with aldehydes and ketones at 0 °C: Concellón, J. M, Cuervo, H, Fernández-Fano, R. Tetrahedron 2001, 57, 8983-8987
    • A synthesis of epoxides has been reported by reaction of iodomethyllithium with aldehydes and ketones at 0 °C: Concellón, J. M.; Cuervo, H.; Fernández-Fano, R. Tetrahedron 2001, 57, 8983-8987.
  • 87
    • 0033056130 scopus 로고    scopus 로고
    • Barluenga, J.; Baragaña, B.; Concellón, J. M.; Piñera-Nicolás, A.; D?́az, M. R.; Garc?́a-Granda, S. J. Org. Chem. 1999, 64, 5048-5052.
    • (i) Barluenga, J.; Baragaña, B.; Concellón, J. M.; Piñera-Nicolás, A.; D?́az, M. R.; Garc?́a-Granda, S. J. Org. Chem. 1999, 64, 5048-5052.
  • 93
    • 64149095006 scopus 로고    scopus 로고
    • Reference 19f
    • (e) Reference 19f.
  • 104
    • 61349184526 scopus 로고    scopus 로고
    • Concellón, J. M.; Rodr?́\guez-Solla, H.; Simal, C. Org. Lett. 2008, 10, 4457-4460.
    • Concellón, J. M.; Rodr?́\guez-Solla, H.; Simal, C. Org. Lett. 2008, 10, 4457-4460.
  • 109
    • 0344391999 scopus 로고    scopus 로고
    • Concellón, J. M. Riego, E.Á lvarez, J. R. J. Org. Chem. 2003, 68, 9242-9246.
    • (b) Concellón, J. M. Riego, E.Á lvarez, J. R. J. Org. Chem. 2003, 68, 9242-9246.
  • 111
    • 10044237878 scopus 로고    scopus 로고
    • Concellón, J. M. Riego, E. Suárez, J. R. Garc?́a-Granda, S. D?́az, M. R. Org. Lett. 2004, 6, 4499-4501.
    • (d) Concellón, J. M. Riego, E. Suárez, J. R. Garc?́a-Granda, S. D?́az, M. R. Org. Lett. 2004, 6, 4499-4501.
  • 113
    • 27744475785 scopus 로고    scopus 로고
    • Concellón, J. M. Bernad, P. L. Suárez, J. R. Garc?́a-Granda, S. D?́az, M. R. J. Org. Chem. 2005, 70, 9411-9416
    • (f) Concellón, J. M. Bernad, P. L. Suárez, J. R. Garc?́a-Granda, S. D?́az, M. R. J. Org. Chem. 2005, 70, 9411-9416
  • 114
    • 64149099771 scopus 로고    scopus 로고
    • Reference 8b
    • (g) Reference 8b.
  • 116
    • 64149093413 scopus 로고    scopus 로고
    • An excess of iodomethyllithium was necessary due to the presence of N-tosylamine in the mixture reaction, as a consequence of the N-sulfinyl-ptoluenesulfonamide required for the synthesis of aminoaldimines 10, which is purchased with a purity of ∼70
    • An excess of iodomethyllithium was necessary due to the presence of N-tosylamine in the mixture reaction, as a consequence of the N-sulfinyl-ptoluenesulfonamide required for the synthesis of aminoaldimines 10, which is purchased with a purity of ∼70%.
  • 117
    • 0000341555 scopus 로고    scopus 로고
    • The determination of the absence of raeemization was carried out with the phenylalaninal, due to its high proclivity to racemize: Rittle, K. E.; Homnick, C. F.; Ponciello, G. S.; Evans, B. E. J. Ors. Chem. 1982, 47, 3016-3018.
    • The determination of the absence of raeemization was carried out with the phenylalaninal, due to its high proclivity to racemize: Rittle, K. E.; Homnick, C. F.; Ponciello, G. S.; Evans, B. E. J. Ors. Chem. 1982, 47, 3016-3018.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.