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Volumn 6, Issue 24, 2004, Pages 4503-4505

Sulfonimidamides: Efficient chiral iminoiodane precursors for diastereoselective copper-catalyzed aziridination of olefins

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZENE DERIVATIVE; COPPER; IMINE; IODINE DERIVATIVE; SULFONAMIDE; TOLUENESULFONAMIDE DERIVATIVE;

EID: 10044280513     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048167a     Document Type: Article
Times cited : (95)

References (50)
  • 13
    • 2342468596 scopus 로고    scopus 로고
    • For recent examples, see: (a) White, R. D.; Keaney, G. F.; Slown, C. D.; Wood, J. L. Org. Lett. 2004, 6, 1123-1126. (b) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.
    • (2004) Org. Lett. , vol.6 , pp. 1123-1126
    • White, R.D.1    Keaney, G.F.2    Slown, C.D.3    Wood, J.L.4
  • 14
    • 0141534438 scopus 로고    scopus 로고
    • For recent examples, see: (a) White, R. D.; Keaney, G. F.; Slown, C. D.; Wood, J. L. Org. Lett. 2004, 6, 1123-1126. (b) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11510-11511
    • Hinman, A.1    Du Bois, J.2
  • 29
    • 10044260312 scopus 로고    scopus 로고
    • Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M.
    • (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M.
  • 32
    • 1542318994 scopus 로고    scopus 로고
    • Initial experiments with chiral sulfinamides failed since these sulfur-(IV) reagents did not survive the oxidizing conditions of the PhI=O-mediated aziridination. See also: Leca, D.; Song, K.; Amatore, M.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. Eur. J. 2004, 10, 906-916.
    • (2004) Chem. Eur. J. , vol.10 , pp. 906-916
    • Leca, D.1    Song, K.2    Amatore, M.3    Fensterbank, L.4    Lacôte, E.5    Malacria, M.6
  • 47
    • 10044278635 scopus 로고    scopus 로고
    • See ref 18e
    • Both enantiomers of sulfonimidamide 1 are accessible by resolution using (S)- or (R)-α-methylbenzylamine. See ref 18e.
  • 48
    • 1542375289 scopus 로고    scopus 로고
    • Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 49
    • 6444230448 scopus 로고    scopus 로고
    • During the submission of this manuscript, a paper has appeared where the use of N-(benzoyl)sulfonimidamides for copper-mediated nitrene transfer is described. See: Leca, D.; Toussaint, A.; Mareau, C.; Fensterbank, L.; Lacôte, E.; Malacria, M. Org. Lett. 2004, 6, 3573-3575.
    • (2004) Org. Lett. , vol.6 , pp. 3573-3575
    • Leca, D.1    Toussaint, A.2    Mareau, C.3    Fensterbank, L.4    Lacôte, E.5    Malacria, M.6
  • 50
    • 10044284790 scopus 로고    scopus 로고
    • See ref 18e
    • In this context, it should be mentioned that the N-(p-toluenesulfonyl)-p- toluenesulfonimidoyl group may be cleaved under reductive conditions, i.e., by using sodium naphthanelide. See ref 18e.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.