One-Pot Tandem Approach to Spirocyclic Oxindoles Featuring Adjacent Spiro-Stereocenters

被引：208
|
作者：
Liu, Yun-Lin [1 ]
Wang, Xin [2 ]
Zhao, Yu-Lei [1 ]
Zhu, Feng [1 ]
Zeng, Xing-Ping [1 ]
Chen, Long [1 ]
Wang, Cui-Hong [1 ]
Zhao, Xiao-Li [1 ]
Zhou, Jian [1 ]
机构：
[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[2] Sichuan Univ, Coll Chem, Chengdu 610064, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 51期
关键词：
asymmetric catalysis; heterocycles; organocatalysis; spiro compounds; synthetic methods; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; BAYLIS-HILLMAN CARBONATES; 3+2 ANNULATION; ENANTIOSELECTIVE CONSTRUCTION; QUATERNARY STEREOCENTERS; EFFICIENT CONSTRUCTION; CONJUGATE ADDITION; CONCISE SYNTHESIS; ALLYLIC COMPOUNDS; HIGHLY EFFICIENT;
D O I：
10.1002/anie.201307250
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：13735 / 13739
页数：5
相关论文
共 50 条
  • [21] Sequential one-pot synthesis of N-sulfonyl spiroaziridine oxindoles from spiroepoxy oxindoles
    Biswas, Anurag
    Abu Saleh, S. K.
    Hazra, Atanu
    Debnath, Subhas Chandra
    Hajra, Saumen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (25) : 5624 - 5631
  • [22] One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening
    Nimmo, Alastair J.
    Kasten, Kevin
    White, George
    Roeterdink, Julia
    McKay, Aidan P.
    Cordes, David B.
    Smith, Andrew David
    MOLECULES, 2024, 29 (15):
  • [23] Asymmetric Triple Relay Catalysis: Enantioselective Synthesis of Spirocyclic Indolines through a One-Pot Process Featuring an Asymmetric 6π Electrocyclization
    Yin, Xiao-Ping
    Zeng, Xing-Ping
    Liu, Yun-Lin
    Liao, Fu-Min
    Yu, Jin-Sheng
    Zhou, Feng
    Zhou, Jian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) : 13740 - 13745
  • [24] ORGN 199-Catalyst-free one-pot regio and diastereoselective synthesis of spiro thio-oxindoles accelerated in water
    Pirani, Parisa
    Moghaddam, Firouz Matloubi
    Taheri, Salman
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [25] One-pot chemo/regio/stereoselective generation of a library of functionalized spiro-oxindoles/pyrrolizines/pyrrolidines from α-aroylidineketene dithioacetals
    Dhanalakshmi, Pandi
    Babu, Seenivasagaperumal Sriram
    Thimmarayaperumal, Solaimalai
    Shanmugam, Sivakumar
    RSC ADVANCES, 2015, 5 (43) : 33705 - 33719
  • [26] Tandem catalysis and self-assembly: A one-pot approach to functionalized polymers
    Pollino, JM
    Weck, M
    ORGANIC LETTERS, 2002, 4 (05) : 753 - 756
  • [27] 'One-pot' reactions: Total synthesis of the spirocyclic marine sesquiterpene, (+)-axenol
    Oesterreich, K
    Klein, I
    Spitzner, D
    SYNLETT, 2002, (10) : 1712 - 1714
  • [28] Synthesis of Spirocyclic β- and γ-Sultams by One-Pot Reductive Cyclization of Cyanoalkylsulfonyl Fluorides
    Stepannikova, Kateryna O.
    Vashchenko, Bohdan V.
    Grygorenko, Oleksandr O.
    Gorichko, Marian, V
    Cherepakha, Artem Yu
    Moroz, Yurii S.
    Volovenko, Yulian M.
    Zhersh, Serhii
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (47) : 6530 - 6540
  • [29] One-pot synthesis of diverse chiral spiro-azetidinepiperidines
    Simila, Suvi T. M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [30] Palladium-Catalyzed One-Pot Approach to 3-(Diarylmethylene)oxindoles from Propiolamidoaryl Triflate
    Lee, Dahye
    Park, Sunhwa
    Yu, Yoseb
    Shin, Kye Jung
    Seo, Jae Hong
    MOLECULES, 2015, 20 (08) : 14022 - 14032
12345