Enantioselective construction of sterically hindered tertiary α-aryl ketones: a catalytic asymmetric synthesis of isoflavanones

被引：29
作者：
Carroll, Michael P. [1 ]
Mueller-Bunz, Helge [1 ]
Guiry, Patrick J. [1 ]
机构：
[1] Univ Coll Dublin, Ctr Synth & Chem Biol, Sch Chem & Chem Biol, Dublin 4, Ireland
来源：
CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 90期
关键词：
CROSS-COUPLINGS; ALLYLIC ALKYLATION; DECARBOXYLATIVE ALLYLATION; ARYLATION; ORGANOLEAD; ACIDITIES; ESTERS;
D O I：
10.1039/c2cc36452b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A method for the catalytic asymmetric alpha-arylation of ketones bearing very sterically hindered aryl rings has been developed. This reaction occurs under mild conditions, in short reaction times and has been applied to the first catalytic asymmetric synthesis of isoflavanones.
引用
收藏
页码：11142 / 11144
页数：3
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共 47 条
  • [1] Asymmetric arylation of ketone enolates
    Ahman, J
    Wolfe, JP
    Troutman, MV
    Palucki, M
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) : 1918 - 1919
  • [2] Enantioselective α-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis
    Allen, Anna E.
    MacMillan, David W. C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) : 4260 - 4263
  • [3] APPLICATION OF ARYLLEAD(IV) DERIVATIVES TO THE PREPARATION OF 3-ARYL-4-HYDROXY-1-BENZOPYRAN-2-ONES
    BARTON, DHR
    DONNELLY, DMX
    FINET, JP
    GUIRY, PJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11): : 1365 - 1375
  • [4] A FACILE SYNTHESIS OF 3-ARYL-4-HYDROXYCOUMARINS
    BARTON, DHR
    DONNELLY, DMX
    FINET, JP
    GUIRY, PJ
    [J]. TETRAHEDRON LETTERS, 1989, 30 (12) : 1539 - 1542
  • [5] TOTAL SYNTHESIS OF ISOROBUSTIN
    BARTON, DHR
    DONNELLY, DMX
    FINET, JP
    GUIRY, PJ
    [J]. TETRAHEDRON LETTERS, 1990, 31 (51) : 7449 - 7452
  • [6] Enantioselective Decarboxylative Alkylation Reactions: Catalyst Development, Substrate Scope, and Mechanistic Studies
    Behenna, Douglas C.
    Mohr, Justin T.
    Sherden, Nathaniel H.
    Marinescu, Smaranda C.
    Harned, Andrew M.
    Tani, Kousuke
    Seto, Masaki
    Ma, Sandy
    Novak, Zoltan
    Krout, Michael R.
    McFadden, Ryan M.
    Roizen, Jennifer L.
    Enquist, John A., Jr.
    White, David E.
    Levine, Samantha R.
    Petrova, Krastina V.
    Iwashita, Akihiko
    Virgil, Scott C.
    Stoltz, Brian M.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (50) : 14199 - 14223
  • [7] Enantioselective α-Arylation of N-Acyloxazolidinones with Copper(II)-bisoxazoline Catalysts and Diaryliodonium Salts
    Bigot, Aurelien
    Williamson, Alice E.
    Gaunt, Matthew J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) : 13778 - 13781
  • [8] ACIDITIES AND HOMOLYTIC BOND-DISSOCIATION ENERGIES OF THE ALPHA-C-H BONDS IN KETONES IN DMSO
    BORDWELL, FG
    HARRELSON, JA
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (10): : 1714 - 1718
  • [9] ACIDITIES OF THE H-C PROTONS IN CARBOXYLIC ESTERS, AMIDES, AND NITRILES
    BORDWELL, FG
    FRIED, HE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) : 4327 - 4331
  • [10] THE CHEMISTRY OF SUBTERRANEAN CLOVER .2. SYNTHESIS AND REDUCTION OF ISOFLAVONES RELATED TO GENISTEIN AND FORMONONETIN
    BRADBURY, RB
    WHITE, DE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1953, (MAR): : 871 - 876
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