Kinetic resolution of axially chiral 2,2′-dihydroxy-1,1′-biaryls by palladium-catalyzed alcoholysis

被引:92
作者
Aoyama, H
Tokunaga, M [1 ]
Kiyosu, J
Iwasawa, T
Obora, Y
Tsuji, Y
机构
[1] Hokkaido Univ, Grad Sch Sci, Catalysis Res Ctr, SORST, Sapporo, Hokkaido 0010021, Japan
[2] Hokkaido Univ, Grad Sch Sci, Div Chem, SORST, Sapporo, Hokkaido 0010021, Japan
[3] Japan Sci & Technol Corp, CREST, Sapporo, Hokkaido 0010021, Japan
关键词
D O I
10.1021/ja051750h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium-diamine complexes catalyzed kinetic resolution of axially chiral 2,2′-dihydroxy-1,1′-biaryls by alcoholysis of vinyl ethers. The reaction proceeded with high selectivity for various kinds of biaryls. This process is applicable to not only binaphthols but also biphenols, which have been considered to be difficult for the enantioselective synthesis by known catalytic methods. Copyright © 2005 American Chemical Society.
引用
收藏
页码:10474 / 10475
页数:2
相关论文
共 26 条
  • [1] Hydrolysis of alkenyl esters and ethers catalyzed by metal complexes
    Aoyama, H
    Tokunaga, M
    Hiraiwa, S
    Shirogane, Y
    Obora, Y
    Tsuji, Y
    [J]. ORGANIC LETTERS, 2004, 6 (04) : 509 - 512
  • [2] Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates
    Barhate, NB
    Chen, CT
    [J]. ORGANIC LETTERS, 2002, 4 (15) : 2529 - 2532
  • [3] Synthesis of allyl and alkyl vinyl ethers using an in situ prepared air-stable palladium catalyst. Efficient transfer vinylation of primary, secondary, and tertiary alcohols
    Bosch, M
    Schlaf, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) : 5225 - +
  • [4] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents
    Bringmann, G
    Breuning, M
    Tasler, S
    [J]. SYNTHESIS-STUTTGART, 1999, (04): : 525 - 558
  • [5] BINOL: A versatile chiral reagent
    Brunel, JM
    [J]. CHEMICAL REVIEWS, 2005, 105 (03) : 857 - 897
  • [6] Chiral nonracemic C2-symmetric biphenyls by desymmetrization of 6,6′,2,2′-tetramethoxy-1,1′-biphenyl
    Delogu, G
    Fabbri, D
    Dettori, MA
    Forni, A
    Casalone, G
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (21) : 4417 - 4427
  • [7] Copper(I)-catalyzed asymmetric oxidative coupling polymerization of 2,3-dihydroxynaphthalene using bisoxazoline ligands
    Habaue, S
    Seko, T
    Okamoto, Y
    [J]. MACROMOLECULES, 2003, 36 (08) : 2604 - 2608
  • [8] Irie R, 2000, SYNLETT, P1433
  • [9] Homogeneous palladium catalyst suppressing Pd black formation in air oxidation of alcohols
    Iwasawa, T
    Tokunaga, M
    Obora, Y
    Tsuji, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) : 6554 - 6555
  • [10] Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4