Studies into diastereoselective Dotz benzannulations for the synthesis of axially chiral biaryls

被引:11
作者
Anderson, JC [1 ]
Cran, JW
King, NP
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/j.tetlet.2003.08.096
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of racemic chiral ortho substituents on 1-phenythex-1-yne have been found to control the atroposelective formation of a biaryl from Dotz benzannulation with pentacarbonyl(methoxyphenylmethylene)chromium(0). The results show there is a subtle balance between the chiral ortho substituent controlling atroposelectivity with a dr 3-5:1 and allowing benzannulation to proceed in yields of 44-67%. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7771 / 7774
页数:4
相关论文
共 38 条
  • [1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS
    ALEXAKIS, A
    MANGENEY, P
    [J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (08) : 477 - 511
  • [2] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE
    AMATORE, C
    BLART, E
    GENET, JP
    JUTAND, A
    LEMAIREAUDOIRE, S
    SAVIGNAC, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6829 - 6839
  • [3] Steric and electronic limitations for the Dotz benzannulation of aromatic alkynes
    Anderson, JC
    Cran, JW
    King, NP
    [J]. TETRAHEDRON LETTERS, 2002, 43 (21) : 3849 - 3852
  • [4] Investigations into ambient temperature biaryl coupling reactions
    Anderson, JC
    Namli, H
    Roberts, CA
    [J]. TETRAHEDRON, 1997, 53 (44) : 15123 - 15134
  • [5] Reaction of Fischer carbene complexes with 1,3-butadiynes: A new strategem for biaryl synthesis with construction of the biaryl bond preceding synthesis of the arenes
    Bao, JM
    Wulff, WD
    Fumo, MJ
    Grant, EB
    Heller, DP
    Whitcomb, MC
    Yeung, SM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) : 2166 - 2181
  • [6] Stereoselective total synthesis of axially chiral natural products via biaryl lactones
    Bringmann, G
    Menche, D
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) : 615 - 624
  • [7] 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
  • [8] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES
    BRINGMANN, G
    WALTER, R
    WEIRICH, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09): : 977 - 991
  • [9] The first asymmetric Suzuki cross-coupling reaction
    Cammidge, AN
    Crépy, KVL
    [J]. CHEMICAL COMMUNICATIONS, 2000, (18) : 1723 - 1724
  • [10] Asymmetric Suzuki cross-coupling reaction: chirality reversal depending on the palladium-chiral phosphine ratio
    Castanet, AS
    Colobert, F
    Broutin, PE
    Obringer, M
    [J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (06) : 659 - 665