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Volumn 131, Issue 35, 2009, Pages 12560-12561

Oxaziridine-mediated intramolecular amination of sp3-hybridized c-h bonds

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND; CHEMICAL EQUATIONS; INTRAMOLECULAR AMINATION; INTRAMOLECULAR CYCLIZATIONS; NITROGEN-CONTAINING HETEROCYCLES; OXAZIRIDINES; RAPID CONSTRUCTION; TETRAHYDROISOQUINOLINES;

EID: 69849109789     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906183g     Document Type: Article
Times cited : (50)

References (27)
  • 1
    • 6044269298 scopus 로고
    • For reviews of dioxirane reactivity, see: (a)
    • For reviews of dioxirane reactivity, see: (a) Murray, R. W. Chem. Rev. 1989, 89, 1187.
    • (1989) Chem. Rev. , vol.89 , pp. 1187
    • Murray, R.W.1
  • 4
    • 0000960640 scopus 로고
    • For reviews of oxaziridine reactivity, see: (a)
    • For reviews of oxaziridine reactivity, see: (a) Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703.
    • (1989) Tetrahedron , vol.45 , pp. 5703
    • Davis, F.A.1    Sheppard, A.C.2
  • 20
    • 11844258782 scopus 로고    scopus 로고
    • The ability of a Lewis acid to increase the oxygen atom transfer capability of an N-alkyl oxaziridine has been reported
    • The ability of a Lewis acid to increase the oxygen atom transfer capability of an N-alkyl oxaziridine has been reported: Schoumacker, S.; Hamelin, O.; Téti, S.; Pécaut, J.; Fontecave, M. J. Org. Chem. 2005, 70, 301.
    • (2005) J. Org. Chem. , vol.70 , pp. 301
    • Schoumacker, S.1    Hamelin, O.2    Téti, S.3    Pécaut, J.4    Fontecave, M.5
  • 26
    • 33846283043 scopus 로고    scopus 로고
    • No other products of C-H amination were observed; the mass balance in these experiments consisted of the isomeric N-sulfonylated amides, analogous to the products of Aubé's copper(I)-catalyzed rearrangements of oxaziridines. See
    • No other products of C-H amination were observed; the mass balance in these experiments consisted of the isomeric N-sulfonylated amides, analogous to the products of Aubé's copper(I)-catalyzed rearrangements of oxaziridines. See: Aubé, J. Chem. Soc. Rev. 1997, 26, 269.
    • (1997) Chem. Soc. Rev. , vol.26 , pp. 269
    • Aubé, J.1
  • 27
    • 69849092939 scopus 로고    scopus 로고
    • note
    • Attempts to perform aminations of primary and tertiary C-H bonds have not been successful. We attribute these results to the greater bond strength of primary C-H bonds and the congested steric environment of tertiary C-H bonds.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.