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Volumn 11, Issue 7, 2009, Pages 1543-1546

Diastereoselective room-temperature Pd-catalyzed α-arylation and vinylation of arylmandelic acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; FUSED HETEROCYCLIC RINGS; MANDELIC ACID DERIVATIVE; PALLADIUM;

EID: 64349102341     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900131q     Document Type: Article
Times cited : (19)

References (52)
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    • Selected examples in enantioselective construction of quaternary centers: (a) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. A. Eur. J. Org. Chem. 2007, 5969.
  • 6
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    • Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley & Sons: New York, 2000; Chapter 8E.
    • (f) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley & Sons: New York, 2000; Chapter 8E.
  • 7
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    • Donde, Y.; Overman, L. E. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley & Sons: New York, 2000; Chapter 8G.
    • (g) Donde, Y.; Overman, L. E. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley & Sons: New York, 2000; Chapter 8G.
  • 8
    • 0037393778 scopus 로고    scopus 로고
    • Selected reviews in α-arylation of carbonyl compounds: (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
    • Selected reviews in α-arylation of carbonyl compounds: (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
  • 10
    • 0032481653 scopus 로고    scopus 로고
    • Selected references on R-arylation of ketones: (a) Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918.
    • Selected references on R-arylation of ketones: (a) Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918.
  • 17
    • 44449165126 scopus 로고    scopus 로고
    • Selected references on R-arylation of amino acid derivatives
    • (h) Hama, T.; Hartwig, J. F. Org. Lett. 2008, 10, 1545. Selected references on R-arylation of amino acid derivatives:
    • (2008) Org. Lett , vol.10 , pp. 1545
    • Hama, T.1    Hartwig, J.F.2
  • 19
    • 0034814843 scopus 로고    scopus 로고
    • Selected references on α-arylation of amides
    • (j) Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am Chem. Soc. 2001, 123, 8410. Selected references on α-arylation of amides:
    • (2001) J. Am Chem. Soc , vol.123 , pp. 8410
    • Lee, S.1    Beare, N.A.2    Hartwig, J.F.3
  • 21
    • 33646138279 scopus 로고    scopus 로고
    • Selected references on α-vinylation of ketones
    • (l) Hama, T.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 4976. Selected references on α-vinylation of ketones:
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 4976
    • Hama, T.1    Culkin, D.A.2    Hartwig, J.F.3
  • 22
    • 0037149687 scopus 로고    scopus 로고
    • α-Arylation of aldehydes
    • (m) Hamada, T.; Buchwald, S. L. Org. Lett. 2002, 4, 999. α-Arylation of aldehydes:
    • (2002) Org. Lett , vol.4 , pp. 999
    • Hamada, T.1    Buchwald, S.L.2
  • 34
    • 0030765220 scopus 로고    scopus 로고
    • Kiesewetter, D. O.; Carson, R. E.; Jagoda, E. M.; Endres, C. J.; Der, M. G.; Herscovich, P.; Eckelman, W. C. Bioorg. Med. Chem. 1997, 5, 1555.
    • (b) Kiesewetter, D. O.; Carson, R. E.; Jagoda, E. M.; Endres, C. J.; Der, M. G.; Herscovich, P.; Eckelman, W. C. Bioorg. Med. Chem. 1997, 5, 1555.
  • 46
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    • α-hydroxy acids: (a) Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Synthesis; VCH: Weinheim, 1997. Diols:
    • α-hydroxy acids: (a) Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Synthesis; VCH: Weinheim, 1997. Diols:
  • 49
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    • The synthesis of (S,S)-I is reproductible. See ref 7
    • The synthesis of (S,S)-I is reproductible. See ref 7.
  • 50
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    • Using chiral auxiliaries: see ref 6. Examples of asymmetric intramolecular α-arylation: (a) Fortanet, J.-G, Buchwald, S. L. Angew. Chem, Int. Ed. 2008, 47, 8108
    • Using chiral auxiliaries: see ref 6. Examples of asymmetric intramolecular α-arylation: (a) Fortanet, J.-G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 8108.
  • 51
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    • Jia, X.-Y, Hillgren, J. M:; Watson, L. E, Marsden, S. P, Kündig, E. P. Chem. Commun. 2008, 4040. For examples of nonasymmetric a-arylations: see ref 3j and
    • (b) Jia, X.-Y.; Hillgren, J. M:; Watson, L. E.; Marsden, S. P.; Kündig, E. P. Chem. Commun. 2008, 4040. For examples of nonasymmetric a-arylations: see ref 3j and:


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