Stereoselective Synthesis of Cyclohexanes via an Iridium Catalyzed (5+1) Annulation Strategy

被引：65
作者：
Akhtar, Wasim M. [1 ]
Armstrong, Roly J. [1 ]
Frost, James R. [1 ]
Stevenson, Neil G. [2 ]
Donohoe, Timothy J. [1 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 38期
基金：
英国工程与自然科学研究理事会;
关键词：
HYDROGEN BORROWING CATALYSIS; CARBONYL-COMPOUNDS; C-H; ALCOHOLS; ALKYLATION; AMINES; DEHYDROGENATION; CARBOCYCLES; CARBANIONS; ACCESS;
D O I：
10.1021/jacs.8b07776
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An iridium catalyzed method for the synthesis of functionalized cyclohexanes from methyl ketones and 1,5-diols is described. This process operates by two sequential hydrogen borrowing reactions, providing direct access to multisubstituted cyclic products with high levels of stereocontrol. This methodology represents a novel (5 + 1) strategy for the stereoselective construction of the cyclohexane core.
引用
收藏
页码：11916 / 11920
页数：5
相关论文
共 42 条
  • [1] Hydrogen Borrowing Catalysis with Secondary Alcohols: A New Route for the Generation of β-Branched Carbonyl Compounds
    Akhtar, Wasim M.
    Cheong, Choon Boon
    Frost, James R.
    Christensen, Kirsten E.
    Stevenson, Neil G.
    Donohoe, Timothy J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (07) : 2577 - 2580
  • [2] [Anonymous], 2005, METAL CATALYSED REAC, P437
  • [3] Ansell M. F, 1992, RODDS CHEM CARB COMP, V2
  • [4] The Catalytic Amination of Alcohols
    Baehn, Sebastian
    Imm, Sebastian
    Neubert, Lorenz
    Zhang, Min
    Neumann, Helfried
    Beller, Matthias
    [J]. CHEMCATCHEM, 2011, 3 (12) : 1853 - 1864
  • [5] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane.
    Beesley, RM
    Ingold, CK
    Thorpe, JF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 : 1080 - 1106
  • [6] ELIMINATION AND ADDITION-REACTIONS .40. THE INSIGNIFICANT EFFECT OF STRAIN IN HIGHER-ORDER ELIMINATIONS IN 1,1-BIS(PHENYLSULPHONYL) CARBANIONS WITH OMEGA-LEAVING GROUPS
    BENEDETTI, F
    STIRLING, CJM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (04): : 605 - 611
  • [7] Saturated and partially unsaturated carbocycles
    BookerMilburn, KI
    Sharpe, A
    [J]. CONTEMPORARY ORGANIC SYNTHESIS, 1996, 3 (06): : 473 - 498
  • [8] Discovery and development of tramadol for the treatment of pain
    Bravo, Lidia
    Antonio Mico, Juan
    Berrocoso, Esther
    [J]. EXPERT OPINION ON DRUG DISCOVERY, 2017, 12 (12) : 1281 - 1291
  • [9] ANNELATION STUDIES USING 1,4-DIBROMO AND 1,5-DIBROMO DERIVATIVES IN THE PRESENCE OF CARBANIONS
    CANONNE, P
    PLAMONDON, J
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (03): : 555 - 564
  • [10] Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
12345