메뉴 건너뛰기




Volumn 45, Issue 30, 2006, Pages 4973-4977

Fluorobis(phenylsulfonyl)methane: A fluoromethide equivalent and palladium-catalyzed enantioselective allylic monofluoromethylation

Author keywords

Asymmetric synthesis; Drug design; Fluorine; Fluoromethylation; Palladium

Indexed keywords

ASYMMETRIC SYNTHESIS; DRUG DESIGN; FLUOROMETHYLATION; MONOFLUOROMETHYLATION;

EID: 33746672640     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600625     Document Type: Article
Times cited : (168)

References (75)
  • 1
    • 0003420735 scopus 로고
    • (Eds.: R. Filler, Y. Kobayashi), Elsevier Biomedical Press and Kodansha Ltd, New York
    • a) Biomedicinal Aspects of Fluorine Chemistry (Eds.: R. Filler, Y. Kobayashi), Elsevier Biomedical Press and Kodansha Ltd, New York, 1982;
    • (1982) Biomedicinal Aspects of Fluorine Chemistry
  • 2
    • 0003314351 scopus 로고    scopus 로고
    • Biomedical Frontiers of Fluorine Chemistry
    • b) "Biomedical Frontiers of Fluorine Chemistry": ACS Symp. Ser. 1996, 639;
    • (1996) ACS Symp. Ser. , vol.639
  • 5
    • 0002780706 scopus 로고    scopus 로고
    • Asymmetric Fluoroorganic Chemistry. Synthesis, Applications, and Future Directions
    • b) "Asymmetric Fluoroorganic Chemistry. Synthesis, Applications, and Future Directions": ACS Symp. Ser. 2000, 746;
    • (2000) ACS Symp. Ser. , vol.746
  • 11
    • 33646440717 scopus 로고    scopus 로고
    • d) After submission of this manuscript, the diastereoselective nucleophilic monofluoromethylation of imines with fluoromethyl phenyl sulfone was described: Y. Li, C. Ni, J. Liu, L. Zhang, J. Zheng, L. Zhu, J. Hu, Org. Lett. 2006, 8, 1693-1696.
    • (2006) Org. Lett. , vol.8 , pp. 1693-1696
    • Li, Y.1    Ni, C.2    Liu, J.3    Zhang, L.4    Zheng, J.5    Zhu, L.6    Hu, J.7
  • 12
    • 0004232058 scopus 로고
    • (Eds.: Y. Kobayashi, I. Kumadaki, T. Taguchi), Hirokawa, Tokyo
    • a) Fusso Yakugaku (Eds.: Y. Kobayashi, I. Kumadaki, T. Taguchi), Hirokawa, Tokyo, 1992;
    • (1992) Fusso Yakugaku
  • 19
    • 0002976015 scopus 로고
    • (Eds.: R. Filler, Y. Kobayashi), Elsevier Biomedical Press and Kodansha Ltd, New York, Tokyo
    • b) J. Kollonitsch in Biomedicinal Aspects of Fluorine Chemistry, (Eds.: R. Filler, Y. Kobayashi), Elsevier Biomedical Press and Kodansha Ltd, New York, Tokyo, 1982, pp. 93-122;
    • (1982) Biomedicinal Aspects of Fluorine Chemistry , pp. 93-122
    • Kollonitsch, J.1
  • 24
    • 22144453934 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4204-4207;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4204-4207
  • 31
    • 0035803748 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 4461-4463; .
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4461-4463
  • 33
  • 34
    • 24944543941 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 5882-5886.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5882-5886
  • 43
    • 33746727978 scopus 로고    scopus 로고
    • See the Supporting Information
    • a) See the Supporting Information,
  • 44
    • 33746681569 scopus 로고    scopus 로고
    • note
    • b) A typical experimental procedure is given in the Supporting Information.
  • 46
    • 33746704699 scopus 로고    scopus 로고
    • note
    • a) The reaction mechanism is discussed in the Supporting Information,
  • 47
    • 33746743441 scopus 로고    scopus 로고
    • note
    • b) Absolute stereochemistries were assigned by X-ray crystallographic analysis (for 3d, see the Supporting Information) or tentatively determined by comparing the optical rotations of 3a and 3b with those of their non-fluorinated derivatives (see the Supporting Information);
  • 48
    • 33746697422 scopus 로고    scopus 로고
    • note
    • c) Enantiomeric excesses of 3g,h were determined by HPLC analysis using CHIRALCEL OD-H. The absolute stereochemistry of 3g was assigned based on the proposed reaction mechanism (see reference [10b, f] and the Supporting Information) and tentatively determined by comparing the optical rotation with that of β-D-carbaribofuranose after chemical derivatization of 3g to 5-deoxy-5-fluoro-β-D-carbaribofuranose (5) (see Scheme 3).
  • 65
    • 0032490986 scopus 로고    scopus 로고
    • For example: a) M. T. Crimmins, Tetrahedron 1998, 54, 9229-9272;
    • (1998) Tetrahedron , vol.54 , pp. 9229-9272
    • Crimmins, M.T.1
  • 72
    • 0037131490 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 3913-3915;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3913-3915
  • 75
    • 33746717190 scopus 로고    scopus 로고
    • See reference [18e]
    • 20 = + 10.0 (c = 1.1 in MeOH). See reference [18e].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.