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Volumn 65, Issue 44, 2009, Pages 8987-8994

Enantioselective synthesis of a chiral fluoropiperidine via asymmetric hydrogenation of a vinyl fluoride

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM; FLUORIDE; FLUOROPIPERIDINE; LIGAND; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

EID: 70349321438     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.105     Document Type: Article
Times cited : (32)

References (60)
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    • Ramachandran P.V. (Ed), American Chemical Society, Washington, DC
    • In: Ramachandran P.V. (Ed). Asymmetric Fluoroorganic Chemisry; Synthesis, Applications, and Future Directions. ACS Symposium Series 746 (2000), American Chemical Society, Washington, DC
    • (2000) ACS Symposium Series 746
  • 38
    • 70349329886 scopus 로고    scopus 로고
    • note
    • Reexamining the asymmetric hydrogenation of 2·HCl using catalysts tested in earlier rounds of screening did not result in the identification of any new leads.
  • 39
    • 70349336029 scopus 로고    scopus 로고
    • note
    • 2 and 50 °C overnight led to about 15% conversion to a mix of racemic 1, 6, and debenzylated product(s). In the absence of the wire, no product was formed.
  • 41
    • 38049047508 scopus 로고    scopus 로고
    • For recent examples from these laboratories, see:
    • For recent examples from these laboratories, see:. Shultz C.S., and Krska S.W. Acc. Chem. Res. 40 (2007) 1320-1326
    • (2007) Acc. Chem. Res. , vol.40 , pp. 1320-1326
    • Shultz, C.S.1    Krska, S.W.2
  • 42
    • 0010820910 scopus 로고
    • For a review of transition metal-mediated carbon-fluorine bond activation, including in vinyl fluorides, see:
    • For a review of transition metal-mediated carbon-fluorine bond activation, including in vinyl fluorides, see:. Kiplinger J.L., Richmond T.G., and Osterberg C.E. Chem. Rev. 94 (1994) 373-431
    • (1994) Chem. Rev. , vol.94 , pp. 373-431
    • Kiplinger, J.L.1    Richmond, T.G.2    Osterberg, C.E.3
  • 43
    • 70349333125 scopus 로고    scopus 로고
    • For examples of β-halide elimination processes in early metal systems, see
    • For examples of β-halide elimination processes in early metal systems, see:
  • 50
    • 70349327999 scopus 로고    scopus 로고
    • For recent examples of Rh-mediated defluorination of vinyl fluorides, see
    • For recent examples of Rh-mediated defluorination of vinyl fluorides, see:
  • 54
    • 70349309962 scopus 로고    scopus 로고
    • For examples of Pd-mediated β-halide elimination reactions, see
    • For examples of Pd-mediated β-halide elimination reactions, see:
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    • 70349323042 scopus 로고    scopus 로고
    • note
    • Free des-fluoro olefin was not observed in reactions that were terminated at partial conversion.
  • 59
    • 1542317841 scopus 로고    scopus 로고
    • Base-induced elimination of HX to regenerate a Pd(O)-olefin complex has been observed to occur without decomplexation of the olefin:
    • Base-induced elimination of HX to regenerate a Pd(O)-olefin complex has been observed to occur without decomplexation of the olefin:. Lloyd-Jones G.C., and Slatford P.A. J. Am. Chem. Soc. 126 (2004) 2690-2691
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 2690-2691
    • Lloyd-Jones, G.C.1    Slatford, P.A.2
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    • 70349333124 scopus 로고    scopus 로고
    • The absolute configuration of 1 was determined by conversion to a downstream intermediate with known absolute stereochemistry: Nelson, T.D, Kress, M.H, Krska, S.W, Mitten, J.V, Sun, Y. PCT Int. Appl, WO 2006069287 A1, 2006, CAN 145:103564
    • The absolute configuration of 1 was determined by conversion to a downstream intermediate with known absolute stereochemistry: Nelson, T.D.; Kress, M.H.; Krska, S.W.; Mitten, J.V.; Sun, Y. PCT Int. Appl., WO 2006069287 A1, 2006, CAN 145:103564.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.