Rhodium-catalyzed Michael addition of arylboronic acids to 3-alkylenyloxindoles: asymmetric synthesis of functionalized oxindoles

被引：6
作者：
Zhang, Xiangyang [1 ,2 ,3 ]
Chen, Guihua [1 ,2 ,3 ]
Cao, Peng [1 ]
Liu, Jibing [1 ,2 ,3 ]
Liao, Jian [1 ,2 ]
机构：
[1] Chinese Acad Sci, Nat Prod Res Ctr, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 04期
关键词：
3-Alkylenyoxindoles; Functionalized oxindoles; Arylboronic acids; Michael addition; ENANTIOSELECTIVE SYNTHESIS; SPIROCYCLIC OXINDOLES; ALKENYLBORONIC ACIDS; 1,4-ADDITION; CONSTRUCTION; PEROPHORAMIDINE; HYDROXYLATION; FLUORINATION; DERIVATIVES; 2-OXINDOLES;
D O I：
10.1016/j.tetlet.2011.11.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The rhodium-catalyzed diastereo- and enantioselective Michael addition of arylboronic acids to 3-alkyl-enyloxindoles has been developed with (R)-binap as a ligand. A wide variety of the desired functionalized oxindoles are smoothly obtained in high yields (up to 99%) with high enantioselectivities (up to 92% ee) and good diastereoselectivities (up to 82:18). (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：438 / 441
页数：4
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  • [1] Synthesis of Functionalized Spiroaziridine-oxindoles from 3-Ylideneoxindoles: An Easy Route to 3-(Aminoalkyl)oxindoles
    Ammetto, I.
    Gasperi, T.
    Loreto, M. Antonietta
    Migliorini, A.
    Palmarelli, F.
    Tardella, P. Antonio
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) : 6189 - 6197
  • [2] An approach to the total synthesis of the marine ascidian metabolite perophoramidine via a halogen-selective tandem Heck/carbonylation strategy
    Artman, GD
    Weinreb, SM
    [J]. ORGANIC LETTERS, 2003, 5 (09) : 1523 - 1526
  • [3] Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles
    Bella, M
    Kobbelgaard, S
    Jorgensen, KA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3670 - 3671
  • [4] Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters
    Bencivenni, Giorgio
    Wu, Li-Yuan
    Mazzanti, Andrea
    Giannichi, Berardino
    Pesciaioli, Fabio
    Song, Mao-Ping
    Bartoli, Giuseppe
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) : 7200 - 7203
  • [5] A C2-Symmetric Chiral Bis-Sulfoxide Ligand in a Rhodium-Catalyzed Reaction: Asymmetric 1,4-Addition of Sodium Tetraarylborates to Chromenones
    Chen, Jun
    Chen, Junmin
    Lang, Feng
    Zhang, Xiangyang
    Cun, Linfeng
    Zhu, Jin
    Deng, Jingen
    Liao, Jian
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (13) : 4552 - +
  • [6] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity
    Chen, Xiao-Hua
    Wei, Qiang
    Luo, Shi-Wei
    Xiao, Han
    Gong, Liu-Zhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) : 13819 - 13825
  • [7] Enantioselective Organocatalytic anti-Mannich-Type Reaction of N-Unprotected 3-Substituted 2-Oxindoles with Aromatic N-Ts-aldimines
    Cheng, Liang
    Liu, Li
    Jia, Han
    Wang, Dong
    Chen, Yong-Jun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) : 4650 - 4653
  • [8] The chemistry of isatins: a review from 1975 to 1999
    da Silva, JFM
    Garden, SJ
    Pinto, AC
    [J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (03) : 273 - 324
  • [9] Potassium trifluoro(organo)borates: New perspectives in organic chemistry
    Darses, S
    Genet, JP
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) : 4313 - 4327
  • [10] AcOLeDMAP and BnOLeDMAP: Conformationally Restricted Nucleophilic Catalysts for Enantioselective Rearrangement of Indolyl Acetates and Carbonates
    Duffey, Trisha A.
    Shaw, Scott A.
    Vedejs, Edwin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (01) : 14 - +
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