메뉴 건너뛰기




Volumn 5, Issue 8, 2010, Pages 1875-1883

Rapid and slow generation of 1-trifluoromethylvinyllithium: syntheses and applications of CF3-containing allylic alcohols, allylic amines, and vinyl ketones

Author keywords

Allylic compounds cyclization; Fluorine; Ketones; Lithium

Indexed keywords

ALLYL ALCOHOLS; ALLYLIC ALCOHOL; ALLYLIC AMINES; ALLYLIC COMPOUNDS; ALLYLIC COMPOUNDS CYCLIZATION; CYCLOPENTENONES; ELECTROPHILES; EXCHANGE REACTION; GOOD YIELD; HALOGEN EXCHANGE; IN-SITU; NAZAROV CYCLIZATION; PAUSON-KHAND REACTIONS; SULFOAMIDES; THERMALLY UNSTABLE; TRIFLUOROMETHYL; VINYL KETONES; VINYLATION;

EID: 77955184389     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000139     Document Type: Article
Times cited : (27)

References (102)
  • 9
    • 0034595676 scopus 로고    scopus 로고
    • For a review, see
    • For a review, see: P. Lin, J. Jiang, Tetrahedron 2000, 56, 3635-3671.
    • (2000) Tetrahedron. , vol.56 , pp. 3635-3671
    • Lin, P.1    Jiang, J.2
  • 10
    • 17144368056 scopus 로고    scopus 로고
    • For examples, see: a
    • For examples, see: a) H. Ito, Adv. Polym. Sci. 2005, 172, 37-245;
    • (2005) Adv. Polym. Sci. , vol.172 , pp. 37-245
    • Ito, H.1
  • 14
    • 0000729721 scopus 로고
    • Y = Ph
    • A. E. Feiring, J. Org. Chem. 1980, 45, 1962-1964; [Y = Ph]:
    • (1980) J. Org. Chem. , vol.45 , pp. 1962-1964
    • Feiring, A.E.1
  • 20
    • 53549135785 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4870-4873;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4870-4873
  • 30
    • 0037118361 scopus 로고    scopus 로고
    • references therein
    • H. Lebel, V. Paquet, Org. Lett. 2002, 4, 1671-1674 and references therein;
    • (2002) Org. Lett. , vol.4 , pp. 1671-1674
    • Lebel, H.1    Paquet, V.2
  • 49
    • 34047194290 scopus 로고    scopus 로고
    • For recent reports on the synthesis of 1-trifluoromethyl-1-alkenes 2-trifluoromethyl vinyl compounds, see: a
    • For recent reports on the synthesis of 1-trifluoromethyl-1-alkenes [2-(trifluoromethyl) vinyl compounds], see: a) I. Nowak, M. J. Robins, J. Org. Chem. 2007, 72, 2678-2681;
    • (2007) J. Org. Chem. , vol.72 , pp. 2678-2681
    • Nowak, I.1    Robins, M.J.2
  • 67
    • 77955196141 scopus 로고    scopus 로고
    • When the 1:1 mixture of 2 and nBuLi was kept at-100°C for 15 min and then treated with benzaldehyde, alcohol 5, and 1-phenylpentan-1-ol, the adducts of vinyllithium 1 and nBuLi were obtained in 25 % and 64 % yields, respectively
    • When the 1:1 mixture of 2 and nBuLi was kept at-100°C for 15 min and then treated with benzaldehyde, alcohol 5, and 1-phenylpentan-1-ol, the adducts of vinyllithium 1 and nBuLi were obtained in 25 % and 64 % yields, respectively.
  • 68
    • 0001470788 scopus 로고
    • 19FNMR chemical shifts; a
    • 19FNMR chemical shifts; a) M. Hanack, J. Ullmann, J. Org. Chem. 1989, 54, 1432-1435;
    • (1989) J. Org. Chem. , vol.54 , pp. 1432-1435
    • Hanack, M.1    Ullmann, J.2
  • 69
    • 77955224838 scopus 로고    scopus 로고
    • Ref. 17
    • Ref. [17].
  • 70
    • 38349112396 scopus 로고    scopus 로고
    • For example, see: a, and references therein
    • For example, see: a) S. Nag, S. Madapa, S. Batra, Synthesis 2008, 101-109 and references therein;
    • (2008) Synthesis , pp. 101-109
    • Nag, S.1    Madapa, S.2    Batra, S.3
  • 77
    • 0038587652 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 2060-2063;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 2060-2063
  • 86
    • 24944569905 scopus 로고    scopus 로고
    • For recent reviews on the Pauson-Khand reaction, see: a
    • For recent reviews on the Pauson-Khand reaction, see: a) S. E. Gibson, M. Mainolfi, Angew. Chem. 2005, 117, 3082-3097;
    • (2005) Angew. Chem. , vol.117 , pp. 3082-3097
    • Gibson, S.E.1    Mainolfi, M.2
  • 87
    • 18844403627 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3022-3037;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3022-3037
  • 90
    • 0038665161 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1800-1810.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1800-1810
  • 93
    • 77955180950 scopus 로고    scopus 로고
    • CCDC 772077 contains the supplementary crystallographic data for compound 16. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at
    • CCDC 772077 contains the supplementary crystallographic data for compound 16. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data-request/cif.
  • 94
    • 21844434234 scopus 로고    scopus 로고
    • For recent reviews on the Nazarov cyclization, see: a
    • For recent reviews on the Nazarov cyclization, see: a) A. J. Frontiera, C. Collison, Tetrahedron 2005, 61, 7577-7606;
    • (2005) Tetrahedron. , vol.61 , pp. 7577-7606
    • Frontiera, A.J.1    Collison, C.2
  • 99
    • 0001626918 scopus 로고
    • references therein
    • T. Umemoto, K. Adachi, J. Org. Chem. 1994, 59, 5692-5699 and references therein.
    • (1994) J. Org. Chem. , vol.59 , pp. 5692-5699
    • Umemoto, T.1    Adachi, K.2
  • 100
    • 33747397597 scopus 로고    scopus 로고
    • For recent reports on the cationic reactions conducted in HFIP, see: a, and references therein
    • For recent reports on the cationic reactions conducted in HFIP, see: a) T. Saitoh, S. Yoshida, J. Ichikawa, J. Org. Chem. 2006, 71, 6414-6419 and references therein;
    • (2006) J. Org. Chem. , vol.71 , pp. 6414-6419
    • Saitoh, T.1    Yoshida, S.2    Ichikawa, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.