Atroposelective synthesis of axially chiral biaryl compounds

被引:1192
作者
Bringmann, G [1 ]
Mortimer, AJP
Keller, PA
Gresser, MJ
Garner, J
Breuning, M
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Wollongong, Dept Chem, Wollongong, NSW 2522, Australia
关键词
asymmetric synthesis; atropisomerism; axial chirality; biaryl compounds; stereoselectivity;
D O I
10.1002/anie.200462661
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rotationally hindered and thus stereogenic biaryl axis is the structurally and stereochemically decisive element of a steadily growing number of natural products, chiral auxiliaries, and catalysts. Thus, it is not surprising that significant advances have been made in the asymmetric synthesis of axially chiral biaryl compounds over the past decade. In addition to the classic approach (direct stereoselective aryl-aryl coupling), innovative concepts have been developed in which the asymmetric information is introduced into a preformed, but achiral - that is, symmetric or configurationally labile - biaryl compound, or in which an aryl-C single bond is stereoselectively transformed into an axis. This Review classifies these strategies according to their underlying concepts and critically evaluates their scope and limitations with reference to selected model reactions and applications. Furthermore, the preconditions required for the existence of axial chirality in biaryl compounds are discussed. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5384 / 5427
页数:44
相关论文
共 392 条
  • [21] 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
  • [22] A novel 1,3-central-to-axial chirality induction approach to cyclooctadiene lignans
    Baudoin, O
    Décor, A
    Cesario, M
    Guéritte, F
    [J]. SYNLETT, 2003, (13) : 2009 - 2012
  • [23] Asymmetric catalysis with the normally unresolvable, conformationally dynamic 2,2′-bis(diphenylphosphino)-1,1′-biphenyl (biphep)
    Becker, JJ
    White, PS
    Gagné, MR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) : 9478 - 9479
  • [24] (S)-[3.3'-2H2]BIMESITYL
    BLOCH, M
    ZAHORSZKY, UI
    LAU, N
    MUSSO, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (06): : 1790 - +
  • [25] Vaulted biaryls: Efficient ligands for the aluminum-catalyzed asymmetric Baeyer-Villiger reaction
    Bolm, C
    Frison, JC
    Zhang, Y
    Wulff, WD
    [J]. SYNLETT, 2004, (09) : 1619 - 1621
  • [26] STERIC EFFECTS - A STUDY OF A RATIONALLY DESIGNED SYSTEM
    BOTT, G
    FIELD, LD
    STERNHELL, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) : 5618 - 5626
  • [27] ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS
    BOYD, MR
    HALLOCK, YF
    MANFREDI, KP
    BLUNT, JW
    MCMAHON, JB
    BUCKHEIT, RW
    BRINGMANN, G
    SCHAFFER, M
    CRAGG, GM
    THOMAS, DW
    JATO, JG
    CARDELLINA, JH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) : 1740 - 1745
  • [28] BRINGMANN G, 1994, SYNLETT, P423
  • [29] The 'lactone method':: enantioselective preparation of novel P,N-biaryl ligands and their use in the synthesis of the biarylic alkaloids, ancistrotanzanine B and ancistroealaine A
    Bringmann, G
    Pfeifer, RM
    Schreiber, P
    Hartner, K
    Schraut, M
    Breuning, M
    [J]. TETRAHEDRON, 2004, 60 (20) : 4349 - 4360
  • [30] Atropo-enantioselective synthesis of an axially chiral C1-symmetric phosphine ligand and its application in the asymmetric hydrosilylation of styrenes
    Bringmann, G
    Wuzik, A
    Breuning, M
    Henschel, P
    Peters, K
    Peters, EM
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (15) : 3025 - 3031