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Volumn 129, Issue 7, 2007, Pages 1866-1867

Copper(II)-catalyzed aminohydroxylation of olefins

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; COPPER; EPOXIDE; HYDROXYL GROUP; OSMIUM; OXAZIRIDINE DERIVATIVE; PALLADIUM;

EID: 33847298540     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067894t     Document Type: Article
Times cited : (162)

References (18)
  • 9
  • 10
    • 11844258782 scopus 로고    scopus 로고
    • The activation of an N-alkyl oxaziridine toward sulfoxidation using a stoichiometric zinc(II) additive has been reported: Schoumacker, S.; Hamelin, O.; Teti, S.; Pecaut, J.; Fontecave, M. J. Org. Chem. 2005, 70, 301-308.
    • The activation of an N-alkyl oxaziridine toward sulfoxidation using a stoichiometric zinc(II) additive has been reported: Schoumacker, S.; Hamelin, O.; Teti, S.; Pecaut, J.; Fontecave, M. J. Org. Chem. 2005, 70, 301-308.
  • 12
    • 33847316343 scopus 로고    scopus 로고
    • 2 as a catalyst leads to higher diastereoselectivities, presumably by Lewis acid-catalyzed epimerization of the aminal stereocenter, albeit with diminished yields.
    • 2 as a catalyst leads to higher diastereoselectivities, presumably by Lewis acid-catalyzed epimerization of the aminal stereocenter, albeit with diminished yields.
  • 13
    • 33847256750 scopus 로고    scopus 로고
    • Among additives screened, HMPA provided the fastest rates of reaction, but less toxic ligands can be used instead. For example, aminohydroxylation of styrene proceeds in 81% and 89% yield using 5 mol % of DMPU and pyridine, respectively (see Supporting Information).
    • Among additives screened, HMPA provided the fastest rates of reaction, but less toxic ligands can be used instead. For example, aminohydroxylation of styrene proceeds in 81% and 89% yield using 5 mol % of DMPU and pyridine, respectively (see Supporting Information).
  • 14
    • 33847324330 scopus 로고    scopus 로고
    • 2O (4 h, 80 °C, 95% yield; see Supporting Information).
    • 2O (4 h, 80 °C, 95% yield; see Supporting Information).
  • 16
    • 33847278266 scopus 로고    scopus 로고
    • We have not observed regioisomeric aminal products in the aminohydroxylations of any styrenic olefins investigated to date
    • We have not observed regioisomeric aminal products in the aminohydroxylations of any styrenic olefins investigated to date.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.