메뉴 건너뛰기




Volumn 132, Issue 10, 2010, Pages 3268-3269

Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SYSTEM; CHIRAL AMINES; CHIRAL LEWIS ACID; ENANTIOSELECTIVE; FLUORIDE ANIONS; HIGH SELECTIVITY; KINETIC RESOLUTION; MILD REACTION CONDITIONS; NUCLEOPHILIC FLUORINATION; RING OPENING OF EPOXIDE; TERMINAL EPOXIDE;

EID: 77950462376     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja100161d     Document Type: Article
Times cited : (227)

References (30)
  • 1
    • 49449097238 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Hagmann, W. K. J. Med. Chem. 2008, 57, 4359-4369.
    • (2008) J. Med. Chem. , vol.57 , pp. 4359-4369
    • Hagmann, W.K.1
  • 13
    • 33745185347 scopus 로고    scopus 로고
    • A related strategy for asymmetric catalytic fluoride activation of siliconcontaining substrates has been successful. See: (a) Bappert, E.; Muller, P.; Fu, G. C. Chem. Commun. 2006, 2604-2606.
    • (2006) Chem. Commun. , pp. 2604-2606
    • Bappert, E.1    Muller, P.2    Fu, G.C.3
  • 15
    • 77950472712 scopus 로고    scopus 로고
    • See the Supporting Information for more details
    • See the Supporting Information for more details.
  • 16
    • 33645920995 scopus 로고    scopus 로고
    • (-)-Tetramisole-HCl (CAS: 16595-80-5) is available from Aldrich for $4.65/g. For its use as an enantioselective acyl-transfer catalyst, see: Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351-1354.
    • (2006) Org. Lett. , vol.8 , pp. 1351-1354
    • Birman, V.B.1    Li, X.2
  • 27
    • 77950491114 scopus 로고    scopus 로고
    • No improvement in the rate or selectivity of the kinetic resolution was observed using 2 instead of 1
    • No improvement in the rate or selectivity of the kinetic resolution was observed using 2 instead of 1
  • 28
    • 77950484102 scopus 로고    scopus 로고
    • The conditions outlined in eq-1 gave rise to the regioisomeric product
    • The conditions outlined in eq-1 gave rise to the regioisomeric product.
  • 29
    • 77950492763 scopus 로고    scopus 로고
    • Elevated temperatures (>100 °C), prolonged reaction times, and rigorous exclusion of water are typical. See: Haufe, G. Sci. Synth. 2005, 34, 351-360.
    • (2005) Sci. Synth. , vol.34 , pp. 351-360
    • Haufe, G.1
  • 30
    • 20144383282 scopus 로고    scopus 로고
    • and references therein
    • For a review of the role of donor additives to (salen)M-catalyzed epoxidations, see: McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563-1602, and references therein.
    • (2005) Chem. Rev. , vol.105 , pp. 1563-1602
    • McGarrigle, E.M.1    Gilheany, D.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.