Cooperative Catalysis Approach to Intramolecular Hydroacylation

被引:63
作者
Beletskiy, Evgeny V. [1 ]
Sudheer, Ch. [1 ]
Douglas, Christopher J. [1 ]
机构
[1] Univ Minnesota Twin Cities, Dept Chem, Minneapolis, MN 55455 USA
关键词
DIRECT INTERMOLECULAR HYDROACYLATION; PARALLEL KINETIC RESOLUTION; ENANTIOSELECTIVE HYDROFORMYLATION; ASYMMETRIC CATALYSIS; 4+2 CARBOCYCLIZATION; ADDITION-REACTIONS; BOND ACTIVATION; CHIRAL LIGANDS; C-H; ALDEHYDES;
D O I
10.1021/jo300779q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Prior examples of hydroacylation to form six- and seven-membered ring ketones require either embedded chelating groups or other substrate design strategies to circumvent competitive aldehyde decarbonylation. A cooperative catalysis strategy enabled intramolecular hydroacylation of disubstituted alkenes to form seven- and six-membered rings without requiring substrate-embedded chelating groups.
引用
收藏
页码:5884 / 5893
页数:10
相关论文
共 73 条
  • [1] SYNTHESIS OF BIOLOGICAL MARKERS IN FOSSIL-FUELS .2. SYNTHESIS AND C-13 NMR-STUDIES OF SUBSTITUTED INDANS AND TETRALINS
    ADAMCZYK, M
    WATT, DS
    NETZEL, DA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) : 4226 - 4237
  • [2] Synthesis of cyclooctenones using intramolecular hydroacylation
    Aloise, AD
    Layton, ME
    Shair, MD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (50) : 12610 - 12611
  • [3] [Anonymous], 2011, COMMUNICATION 0308
  • [4] Acetylenic vinyllithiums: Consecutive cycloisomerization-[4+2] cycloaddition reactions
    Bailey, WF
    WachterJurcsak, NM
    Pineau, MR
    Ovaska, TV
    Warren, RR
    Lewis, CE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8216 - 8228
  • [5] Asymmetric catalytic intramolecular hydroacylation of 4-substituted pent-4-enals to beta-substituted cyclopentanones
    Barnhart, RW
    McMorran, DA
    Bosnich, B
    [J]. CHEMICAL COMMUNICATIONS, 1997, (06) : 589 - 590
  • [6] ASYMMETRIC CATALYSIS - ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROACYLATION OF 4-PENTENALS USING CHIRAL RHODIUM DIPHOSPHINE CATALYSTS
    BARNHART, RW
    WANG, XQ
    NOHEDA, P
    BERGENS, SH
    WHELAN, J
    BOSNICH, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) : 1821 - 1830
  • [7] Chelation-assisted intramolecular hydroacylation: synthesis of medium ring sulfur heterocycles
    Bendorf, HD
    Colella, CM
    Dixon, EC
    Marchetti, M
    Matukonis, AN
    Musselman, JD
    Tiley, TA
    [J]. TETRAHEDRON LETTERS, 2002, 43 (39) : 7031 - 7034
  • [8] Probing the importance of the hemilabile site of bis(phosphine) monoxide Ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines:: Discovery of new effective chiral Ligands
    Bonnaventure, Isabelle
    Charette, Andre B.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16) : 6330 - 6340
  • [9] Asymmetric catalysis. A comparative study of the mechanisms of intramolecular hydroacylation and hydrosilation
    Bosnich, B
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (10) : 667 - 674
  • [10] Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-Directed Addition of Salicylaldehydes to Homoallylic Sulfides
    Coulter, Matthew M.
    Kou, Kevin G. M.
    Galligan, Baye
    Dong, Vy M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) : 16330 - 16333