Improved synthesis of (±)-4,12-dihydroxy[2.2]paracyclophane and its enantiomeric resolution by enzymatic methods:: Planar chiral (R)- and (S)-phanol

被引:65
作者
Braddock, DC [1 ]
MacGilp, LD
Perry, BG
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England
[2] GlaxoSmithKline Res & Dev Ltd, Proc Chem, Dartford DA1 5AH, Kent, England
关键词
D O I
10.1021/jo020451x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-)-4,12-Dihydroxy[2.2]paracyclophane [(+/-)PHANOL] is readily prepared from [2.2]paracyclophane by an improved synthetic protocol. Enzymatic kinetic resolution of its bis-acetate proceeds with good enantioselection. Separation, hydrolysis, and recrystallization provides both enantiomers of PHANOL in high enantiopurity.
引用
收藏
页码:8679 / 8681
页数:3
相关论文
共 40 条
  • [1] Facile enantioselective synthesis of a key homoallylic alcohol building block for polyketide synthesis:: TiF4-BINOL catalyzed allylsilylation with allyl trimethylsilane
    Bode, JW
    Gauthier, DR
    Carreira, EM
    [J]. CHEMICAL COMMUNICATIONS, 2001, (24) : 2560 - 2561
  • [2] (dppe)Pt(OTf)2 and (R-BINAP)Pt(OTf)2 Lewis acids catalyze the Diels-Alder reaction by different mechanisms
    Brunkan, NM
    Gagné, MR
    [J]. ORGANOMETALLICS, 2002, 21 (08) : 1576 - 1582
  • [3] A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and α,β-unsaturated ketones
    Burk, MJ
    Hems, W
    Herzberg, D
    Malan, C
    Zanotti-Gerosa, A
    [J]. ORGANIC LETTERS, 2000, 2 (26) : 4173 - 4176
  • [4] Cai DW, 1999, ORG SYNTH, V76, P6
  • [5] BINOL-Ti-catalyzed synthesis of tertiary homoallylic alcohols: The first catalytic asymmetric allylation of ketones
    Casolari, S
    D'Addario, D
    Tagliavini, E
    [J]. ORGANIC LETTERS, 1999, 1 (07) : 1061 - 1063
  • [6] CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS
    COSTA, AL
    PIAZZA, MG
    TAGLIAVINI, E
    TROMBINI, C
    UMANIRONCHI, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 7001 - 7002
  • [7] Dai X, 2001, CHINESE J ORG CHEM, V21, P116
  • [8] The first structural characterization of a [2.2]PHANEPHOS -: Transition-metal complex:: Structure of rac-[Pd(4,12-bis(diphenylphosphino)[2.2]paracyclophane)Cl2]
    Dyer, PW
    Dyson, PJ
    James, SL
    Martin, CM
    Suman, P
    [J]. ORGANOMETALLICS, 1998, 17 (20) : 4344 - 4346
  • [9] A highly chemo- and enantio-selective hetero-Diels-Alder reaction catalysed by chiral aluminium complexes
    Graven, A
    Johannsen, M
    Jorgensen, KA
    [J]. CHEMICAL COMMUNICATIONS, 1996, (20) : 2373 - 2374
  • [10] Effects of torsional angles of 2,2'-biaryldiol ligands in asymmetric Diels-Alder reactions of acrylates catalyzed by their titanium complexes
    Harada, T
    Takeuchi, M
    Hatsuda, M
    Ueda, S
    Oku, A
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (09) : 2479 - 2482