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Volumn 4, Issue 17, 2002, Pages 2929-2932

Lanthanide Lewis acid-mediated enantioselective conjugate radical additions

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; FREE RADICAL; LANTHANUM; LIGAND; PROLINE;

EID: 0038168644     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026327h     Document Type: Article
Times cited : (39)

References (55)
  • 5
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    • Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999 32, 163-171. Sibi, M. P.; Rheault, T. R. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P. Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, pp 461-478.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 163-171
    • Sibi, M.P.1    Porter, N.A.2
  • 6
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    • Renaud, P., Sibi, M. P. Eds.; Wiley-VCH: Weinheim
    • Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999 32, 163-171. Sibi, M. P.; Rheault, T. R. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P. Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, pp 461-478.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 461-478
    • Sibi, M.P.1    Rheault, T.R.2
  • 20
    • 0034612973 scopus 로고    scopus 로고
    • For a review, see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. For other reviews in the area, see: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051-2061.
    • (2000) Tetrahedron , vol.56 , pp. 8033-8061
    • Sibi, M.P.1    Manyem, S.2
  • 21
    • 0035126119 scopus 로고    scopus 로고
    • For a review, see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. For other reviews in the area, see: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051-2061.
    • (2001) Synthesis , pp. 171-196
    • Krause, N.1    Hoffmann-Röder, A.2
  • 22
    • 1842580008 scopus 로고    scopus 로고
    • For a review, see: Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. For other reviews in the area, see: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051-2061.
    • (1998) Eur. J. Org. Chem. , pp. 2051-2061
    • Leonard, J.1    Diez-Barra, E.2    Merino, S.3
  • 31
    • 0036625216 scopus 로고    scopus 로고
    • Selected references on the use of lanthanide Lewis acids in enantioselective transformations. (a) Review: Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226.
    • (2002) Chem. Rev. , vol.102 , pp. 2211-2226
    • Inanaga, J.1    Furuno, H.2    Hayano, T.3
  • 37
    • 84872276904 scopus 로고    scopus 로고
    • note
    • The chemical efficiency for these chiral Lewis acid-mediated conjugate additions was low (<50% isolated yields) and the ees were <15%.
  • 38
    • 84872263989 scopus 로고    scopus 로고
    • note
    • 68% ee (10 mol %); 74% ee (20 mol %); 79% ee (30 mol %); 64% ee (40 mol %).
  • 43
    • 84872267671 scopus 로고    scopus 로고
    • note
    • See Supporting Information in ref 6a for details on stereochemical analysis.
  • 45
    • 84872262240 scopus 로고    scopus 로고
    • note
    • Reactions with these ligands were considerably slower. Yields averaged around 70%.
  • 46
    • 0030669121 scopus 로고    scopus 로고
    • For a good evaluation/analysis of product influence in asymmetric Diels-Alder reaction, see: Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551-10552.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10551-10552
    • Heller, D.P.1    Goldberg, D.R.2    Wulff, W.D.3
  • 48
    • 0034692362 scopus 로고    scopus 로고
    • Examples of ether/alcohol/carboxylic acid/amine-type additives in catalysis with lanthanides: (a) Sibi, M. P.; Rheault, T. R. J. Am. Chem. Soc. 2000. 122, 8873-8879.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8873-8879
    • Sibi, M.P.1    Rheault, T.R.2
  • 55
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    • (c) ref 10d
    • (c) ref 10d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.