메뉴 건너뛰기




Volumn 9, Issue 19, 2007, Pages 3809-3811

Iodinane- and metal-free synthesis of N-cyano sulfilimines: Novel and easy access of NH-sulfoximines

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; IMINE; IODINE; METAL; NITROGEN; OXIME; SULFIDE; SULFUR;

EID: 34848854176     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7016577     Document Type: Article
Times cited : (97)

References (44)
  • 1
    • 34848874142 scopus 로고    scopus 로고
    • For examples of sulfoximines as chiral ligands, see
    • For examples of sulfoximines as chiral ligands, see:
  • 12
    • 0031575567 scopus 로고    scopus 로고
    • For the use of sulfoximines as building blocks for pseudopeptides, see: a
    • For the use of sulfoximines as building blocks for pseudopeptides, see: (a) Bolm. C.; Kahmann, J. D.; Moll, G. Tetrahedron Lett. 1997, 38, 1169.
    • (1997) Tetrahedron Lett , vol.38 , pp. 1169
    • Bolm, C.1    Kahmann, J.D.2    Moll, G.3
  • 17
  • 21
    • 2542470498 scopus 로고    scopus 로고
    • For previous contributions on iminations of sulfur compounds, see the following references. Rh-catalyzed: (a) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305. Ag-catalyzed:
    • For previous contributions on iminations of sulfur compounds, see the following references. Rh-catalyzed: (a) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305. Ag-catalyzed:
  • 22
    • 27644493286 scopus 로고    scopus 로고
    • 4983. Metal-free
    • (b) Cho, G. Y.; Bolm, C. Org. Lett. 2005, 7, 4983. Metal-free:
    • (2005) Org. Lett , vol.7
    • Cho, G.Y.1    Bolm, C.2
  • 24
    • 33745697784 scopus 로고    scopus 로고
    • 2349. For comparative metal-catalyzed iminations of sulfoxides, see
    • (d) García Mancheño, O.; Bolm, C. Org. Lett. 2006, 8, 2349. For comparative metal-catalyzed iminations of sulfoxides, see:
    • (2006) Org. Lett , vol.8
    • García Mancheño, O.1    Bolm, C.2
  • 27
    • 34848815910 scopus 로고    scopus 로고
    • For previous synthesis of N-cyanosulfilimines. see
    • For previous synthesis of N-cyanosulfilimines. see:
  • 32
    • 34848830699 scopus 로고    scopus 로고
    • For previous examples of nucleophilic substitution with amides or aromatic amines, see: a, WO 9821178
    • For previous examples of nucleophilic substitution with amides or aromatic amines, see: (a) Ringer, J. W.; Pearson, D. L.; Scott, C. A.; Wallin, A. P.; WO 9821178.
    • Ringer, J.W.1    Pearson, D.L.2    Scott, C.A.3    Wallin, A.P.4
  • 34
    • 34848841173 scopus 로고    scopus 로고
    • US 4484939
    • (c) Tseng, C. P. US 4484939.
    • Tseng, C.P.1
  • 37
    • 34848887678 scopus 로고    scopus 로고
    • (f) Nummy, L. J.; EP 598396.
    • , vol.EP 598396
    • Nummy, L.J.1
  • 40
    • 34848925716 scopus 로고    scopus 로고
    • US 2005215570 A1
    • (i) Hamilton, C. T. US 2005215570 A1.
    • Hamilton, C.T.1
  • 41
    • 34848868408 scopus 로고    scopus 로고
    • J Kislitsyn, P. G.; Kuchero, F. A.; Chukhrov, L. N.; Zlotin, S. G.; Satrikova, Z. A.; Dolgushin, F. M., Russ. Chem. Bull. 2004, 4, 916.
    • J) Kislitsyn, P. G.; Kuchero, F. A.; Chukhrov, L. N.; Zlotin, S. G.; Satrikova, Z. A.; Dolgushin, F. M., Russ. Chem. Bull. 2004, 4, 916.
  • 43
    • 34848892389 scopus 로고    scopus 로고
    • The 2a/3a ratio did not improve when the reaction was carried out at 0 °C (80:20).
    • The 2a/3a ratio did not improve when the reaction was carried out at 0 °C (80:20).
  • 44
    • 34848903548 scopus 로고    scopus 로고
    • When the reaction of 1h was carried out on 10 mmol scale, a 60:40 ratio 2h/3h was observed and sulfilimine 2h was isolated in 50% yield
    • When the reaction of 1h was carried out on 10 mmol scale, a 60:40 ratio 2h/3h was observed and sulfilimine 2h was isolated in 50% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.