Flexible Strategy for Syntheses of Spirooxindoles using Palladium-Catalyzed Carbosilylation and Sakurai-Type Cyclization

被引：53
作者：
Hande, Sudhir M. [1 ]
Nakajima, Motoyuki [1 ]
Kamisaki, Haruhi [1 ]
Tsukano, Chihiro [1 ]
Takemoto, Yoshiji [1 ]
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 07期
关键词：
HIGHLY ENANTIOSELECTIVE SYNTHESIS; SPIROCYCLIC OXINDOLES; NATURAL-PRODUCTS; CONSTRUCTION; DISCOVERY; 1,3-DIENE;
D O I：
10.1021/ol2003447
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The intramolecular carbosilylation of N-[2-(1,3-butenyl)aryl]carbamoyl chloride has been investigated. The reaction with hexamethyldisilane proceeds smoothly in the presence of a catalytic amount of [Pd(eta(3)-allyl)Cl](2) to give oxindoles with an allylsilane functional group in good yield. The subsequent subjection of the products to a Sakurai-type reaction provides more advanced tricyclic spirooxindoles by controlling the stereochemistry of three contiguous stereogenic centers.
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收藏
页码：1828 / 1831
页数：4
相关论文
共 58 条
  • [1] ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661
  • [2] Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO
  • [3] 2-E
  • [4] Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products
    Antonchick, Andrey P.
    Gerding-Reimers, Claas
    Catarinella, Mario
    Schuermann, Markus
    Preut, Hans
    Ziegler, Slava
    Rauh, Daniel
    Waldmann, Herbert
    [J]. NATURE CHEMISTRY, 2010, 2 (09) : 735 - 740
  • [5] Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes
    Beletskaya, Irina
    Moberg, Christina
    [J]. CHEMICAL REVIEWS, 2006, 106 (06) : 2320 - 2354
  • [6] 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
  • [7] A cage-monoterpene indole alkaloid from Alstonia scholaris
    Cai, Xiang-Hai
    Tan, Qin-Gang
    Liu, Ya-Ping
    Feng, Tao
    Du, Zhi-Zhi
    Li, We-Qi
    Luo, Xiao-Dong
    [J]. ORGANIC LETTERS, 2008, 10 (04) : 577 - 580
  • [8] Highly Enantioselective Construction of Spiro[4H-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine
    Chen, Wen-Bing
    Wu, Zhi-Jun
    Pei, Qing-Lan
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    [J]. ORGANIC LETTERS, 2010, 12 (14) : 3132 - 3135
  • [9] 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
  • [10] CONROY H, 1959, TETRAHEDRON LETT, P6
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