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Volumn 136, Issue 25, 2014, Pages 8899-8902

Enantioselective nucleophile-catalyzed synthesis of tertiary alkyl fluorides via the α-Fluorination of ketenes: Synthetic and mechanistic studies

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; FLUORINE; MECHANICS; NUCLEOPHILES;

EID: 84903287319     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5044209     Document Type: Article
Times cited : (75)

References (36)
  • 4
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    • In; De Vries, J. G. Molander, G. A. Evans, P. A. Georg Thieme: Stuttgart, Vol.
    • Gouverneur, V.; Lozano, O. In Science of Synthesis; De Vries, J. G.; Molander, G. A.; Evans, P. A., Eds.; Georg Thieme: Stuttgart, 2011; Vol. 3, p 851.
    • (2011) Science of Synthesis , vol.3 , pp. 851
    • Gouverneur, V.1    Lozano, O.2
  • 28
    • 84859560300 scopus 로고    scopus 로고
    • For reviews of catalytic asymmetric reactions of ketenes, see: In; List, B. Maruoka, K. Georg Thieme: Stuttgart, Vol.
    • For reviews of catalytic asymmetric reactions of ketenes, see: Chen, S.; Salo, E. C.; Kerrigan, N. J. In Science of Synthesis: Asymmetric Organocatalysis; List, B.; Maruoka, K., Eds.; Georg Thieme: Stuttgart, 2012; Vol. 1, p 455.
    • (2012) Science of Synthesis: Asymmetric Organocatalysis , vol.1 , pp. 455
    • Chen, S.1    Salo, E.C.2    Kerrigan, N.J.3
  • 29
    • 64349105617 scopus 로고    scopus 로고
    • For a review of electrophilic N-F fluorinating agents, see
    • For a review of electrophilic N-F fluorinating agents, see: Baudoux, J.; Cahard, D. Org. React. 2007, 69, 347
    • (2007) Org. React. , vol.69 , pp. 347
    • Baudoux, J.1    Cahard, D.2
  • 31
    • 84903288240 scopus 로고    scopus 로고
    • Under our optimized condition, solutions of the ketene and the nucleophile are added dropwise via a syringe pump to a solution of the catalyst and NFSI; Selectfluor reagent is not a suitable substitute for NFSI; the ee of the product is constant during the course of the reaction; an o -tolyl-substituted and a tert -butyl-substituted ketene were not effective reaction partners.
    • Under our optimized condition, solutions of the ketene and the nucleophile are added dropwise via a syringe pump to a solution of the catalyst and NFSI; Selectfluor reagent is not a suitable substitute for NFSI; the ee of the product is constant during the course of the reaction; an o -tolyl-substituted and a tert -butyl-substituted ketene were not effective reaction partners.
  • 32
    • 84903288241 scopus 로고    scopus 로고
    • Both enantiomers of PPY* are available from Strem Chemicals.
    • Both enantiomers of PPY* are available from Strem Chemicals.
  • 35
    • 34447285728 scopus 로고    scopus 로고
    • The catalytic cycle for the Brønsted-acid mode of reactivity parallels the chiral fluorinating agent pathway (substitution of F-catalyst* with H-catalyst* at the bottom of Figure 2)
    • Dai, X.; Nakai, T.; Romero, J. A. C.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 4367). The catalytic cycle for the Brønsted-acid mode of reactivity parallels the chiral fluorinating agent pathway (substitution of F-catalyst* with H-catalyst* at the bottom of Figure 2)
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 4367
    • Dai, X.1    Nakai, T.2    Romero, J.A.C.3    Fu, G.C.4
  • 36
    • 0033516290 scopus 로고    scopus 로고
    • Previously, we have structurally characterized an N -acylpyridinium salt generated through the reaction of a planar-chiral DMAP derivative with an acid chloride
    • Previously, we have structurally characterized an N -acylpyridinium salt generated through the reaction of a planar-chiral DMAP derivative with an acid chloride: Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5091
    • Tao, B.1    Ruble, J.C.2    Hoic, D.A.3    Fu, G.C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.