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Volumn 14, Issue 18, 2003, Pages 2755-2761

Catalytic asymmetric protonation of fluoro-enolic species: Access to optically active 2-fluoro-1-tetralone

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUORO 1 TETRALONE; BENZYL 2 FLUORO 1 TETRALONE 2 CARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; FLUORIDE; PALLADIUM; QUININE; UNCLASSIFIED DRUG;

EID: 1542708026     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00585-8     Document Type: Article
Times cited : (45)

References (47)
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    • For recent examples, see: (a) Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.; Qi, H.; Han, W.; Przeslawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org. Chem. 1998, 63, 2273-2280; (b) Liu, Z.; Shibata, N.; Takeuchi, Y. J. Org. Chem. 2000, 65, 7583-7587; (c) Cahard, D.; Audouard, C.; Plaquevent, J.-C. ; Roques, N. Org. Lett. 2000, 2, 3699-3701; (d) Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 7001-7009; (e) Muñiz, K. Angew. Chem., Int. Ed. 2001, 40, 1653-1656; (f) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; Cahard, D. Angew. Chem., Int. Ed. 2001, 40, 4214-4216; (g) Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68, 2494-2497.
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    • For alkylation, see: (a) Arai, S.; Oku, M.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 6785-6789; (b) Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J.-C.; Cahard, D. Synthesis 2001, 1742-1746; For fluorination, see: (c) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547.
    • (2001) Synthesis , pp. 1742-1746
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  • 14
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    • For alkylation, see: (a) Arai, S.; Oku, M.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 6785-6789; (b) Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J.-C.; Cahard, D. Synthesis 2001, 1742-1746; For fluorination, see: (c) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547.
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    • For diastereoselective syntheses, see: (a) Davis, F. A.; Kasu, P. V. N. Tetrahedron Lett. 1998, 39, 6135-6138; (b) Enders, D.; Faure, S.; Potthoff, M.; Runsink, J. Synthesis 2001, 2307-2319; For photochemical approach, see: (c) Piva, O. Synlett 1994, 729-731.
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    • For diastereoselective syntheses, see: (a) Davis, F. A.; Kasu, P. V. N. Tetrahedron Lett. 1998, 39, 6135-6138; (b) Enders, D.; Faure, S.; Potthoff, M.; Runsink, J. Synthesis 2001, 2307-2319; For photochemical approach, see: (c) Piva, O. Synlett 1994, 729-731.
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    • 0003117458 scopus 로고
    • For diastereoselective syntheses, see: (a) Davis, F. A.; Kasu, P. V. N. Tetrahedron Lett. 1998, 39, 6135-6138; (b) Enders, D.; Faure, S.; Potthoff, M.; Runsink, J. Synthesis 2001, 2307-2319; For photochemical approach, see: (c) Piva, O. Synlett 1994, 729-731.
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    • Furthermore attempted HPLC analysis of 2-fluorocyclohexanone were unsuccessful.
    • Furthermore attempted HPLC analysis of 2-fluorocyclohexanone were unsuccessful.
  • 32
    • 1842602003 scopus 로고    scopus 로고
    • 2/g, carbon type is activated wood (eggshell distribution).
    • 2/g, carbon type is activated wood (eggshell distribution).
  • 33
    • 1842549752 scopus 로고    scopus 로고
    • 2/g, carbon type is wood (uniform distribution).
    • 2/g, carbon type is wood (uniform distribution).
  • 34
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    • 2/g.
    • 2/g.
  • 35
    • 1842602008 scopus 로고    scopus 로고
    • 2/g.
    • 2/g.
  • 36
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    • 2/g.
    • 2/g.
  • 39
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    • 4.
    • 4..
  • 41
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    • Enantioselective Baylis-Hillman reactions have been successful with 28 as promoter. See:
    • Enantioselective Baylis-Hillman reactions have been successful with 28 as promoter. See: Iwabuchi Y., Nakatani M., Yokoyama N., Hatakeyama S. J. Am. Chem. Soc. 121:1999;10219-10220.
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    • Iwabuchi, Y.1    Nakatani, M.2    Yokoyama, N.3    Hatakeyama, S.4
  • 47
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    • No reliable ee value for each diastereomer could be deduced from these chromatograms.
    • No reliable ee value for each diastereomer could be deduced from these chromatograms.


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