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Volumn 130, Issue 20, 2008, Pages 6610-6615

Activation of N-Sulfonyl oxaziridines using copper(II) catalysts: Aminohydroxylations of styrenes and 1,3-dienes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHEMICAL ACTIVATION; FUNCTIONAL GROUPS; FUNCTIONAL POLYMERS; RATE CONSTANTS; STEREOSELECTIVITY;

EID: 43949088503     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800495r     Document Type: Article
Times cited : (131)

References (61)
  • 8
    • 0000960640 scopus 로고
    • For reviews of oxaziridines in synthesis: a
    • For reviews of oxaziridines in synthesis: (a) Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703-5742.
    • (1989) Tetrahedron , vol.45 , pp. 5703-5742
    • Davis, F.A.1    Sheppard, A.C.2
  • 20
    • 33847298540 scopus 로고    scopus 로고
    • A preliminary communication describing some of this work has been published: Michaelis, D. J.; Shaffer, C. J.; Yoon, T. P J. Am. Chem. Soc. 2007, 129, 1866-1867.
    • A preliminary communication describing some of this work has been published: Michaelis, D. J.; Shaffer, C. J.; Yoon, T. P J. Am. Chem. Soc. 2007, 129, 1866-1867.
  • 24
    • 1942501735 scopus 로고    scopus 로고
    • Two papers describing enantioselective Lewis acid-catalyzed reactions involving N-sulfonyl oxaziridines as electrophilic oxygen sources have recently been published; however, the possibility of oxaziridine activation is not discussed in either report: (b) Toullec, P. Y.; Bonaccorsi, C.; Mezzetti, A.; Togni, A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5810-5814.
    • Two papers describing enantioselective Lewis acid-catalyzed reactions involving N-sulfonyl oxaziridines as electrophilic oxygen sources have recently been published; however, the possibility of oxaziridine activation is not discussed in either report: (b) Toullec, P. Y.; Bonaccorsi, C.; Mezzetti, A.; Togni, A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5810-5814.
  • 34
    • 43949122668 scopus 로고    scopus 로고
    • Dmitrienko proposed a similar cationic mechanism to rationalize the uncatalyzed aminohydroxylation of 2,3-dialkylindoles by 1. See ref 9
    • Dmitrienko proposed a similar cationic mechanism to rationalize the uncatalyzed aminohydroxylation of 2,3-dialkylindoles by 1. See ref 9.
  • 37
    • 33846624362 scopus 로고    scopus 로고
    • For copper(I)- and palladium(II)-catalyzed diaminations of dienes mediated by diaziridinones, see: (a) Du, H. F; Zhao, B. G.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762-763.
    • For copper(I)- and palladium(II)-catalyzed diaminations of dienes mediated by diaziridinones, see: (a) Du, H. F; Zhao, B. G.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762-763.
  • 41
    • 43949130502 scopus 로고    scopus 로고
    • Aminohydroxylations of (Z)-1,3-decadiene also maintain the geometric integrity of the non-reacting olefin.
    • Aminohydroxylations of (Z)-1,3-decadiene also maintain the geometric integrity of the non-reacting olefin.
  • 42
    • 0001284872 scopus 로고    scopus 로고
    • The rotational barrier for cis-trans isomerization in allyl cations has been measured to be 18-24 kcalTmol: (a) Schleyer, P. v. R.; Su, T. M.; Saunders, M.; Rosenfeld, J. C. J. Am. Chem. Soc. 1969, 91, 5174-5176.
    • The rotational barrier for cis-trans isomerization in allyl cations has been measured to be 18-24 kcalTmol: (a) Schleyer, P. v. R.; Su, T. M.; Saunders, M.; Rosenfeld, J. C. J. Am. Chem. Soc. 1969, 91, 5174-5176.
  • 48
    • 0001510281 scopus 로고    scopus 로고
    • Diastereoselective epoxidations directed by allylic sulfonamides: (a) Backvall, J.-E.; Oshima, K.; Palermo, R. E.; Sharpless, K. B J. Org. Chem. 1979, 44, 1953-1957.
    • Diastereoselective epoxidations directed by allylic sulfonamides: (a) Backvall, J.-E.; Oshima, K.; Palermo, R. E.; Sharpless, K. B J. Org. Chem. 1979, 44, 1953-1957.
  • 50
    • 0000123367 scopus 로고    scopus 로고
    • Diastereoselective epoxidations directed by homoallylic alcohols: (c) Zurflüh, R.; Wall, E. N.; Siddall, J. B.; Edwards, J. A. J. Am. Chem. Soc. 1968, 90, 6224-6225.
    • Diastereoselective epoxidations directed by homoallylic alcohols: (c) Zurflüh, R.; Wall, E. N.; Siddall, J. B.; Edwards, J. A. J. Am. Chem. Soc. 1968, 90, 6224-6225.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.