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Acta Chimica Sinica >

2014 , Vol. 72 >Issue 7: 836 - 840

DOI: https://doi.org/10.6023/A14040237

Communication

Asymmetric Diels-Alder Reaction of 2-Arylidene-1,3-indanediones with 2-Vinylindoles Catalyzed by a Sc(OTf)3/Bis(oxazoline) Complex：Enantioselective Synthesis of Tetrahydrocarbazole Spiro Indanedione Derivatives

  • Tan Fen ,
  • Chen Jiarong ,
  • Wang Ping ,
  • Xiao Wenjing
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  • a Key Laboratory of Pesticide & Chemical Biology Ministry of Education and College of Chemistry, Central China Normal University, Wuhan, 430079;
    b College of Pharmacy, Hubei University of Chinese Medicine, Wuhan, 430065

Received date: 2014-04-01

  Online published: 2014-05-07

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21072069, 21002036, 21232003, and 21202053) and the National Basic Research Program of China (973 program, 2011CB808600).

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Abstract

Spirocyclic scaffolds are prevalent in numerous naturally occurring products and pharmaceuticals, which exhibit important biological and pharmacological activities. In this communication, a Sc(OTf)3/Bis(oxazoline) complex catalyzed asymmetric Diels-Alder reaction of 2-arylidene-1,3-indanediones with 2-vinylindoles has been developed. The reaction provides a convenient and practical approach to biologically useful and synthetically important spiro-tetrahydrocarbazoles in good yields with high enantioselectivities (16 examples, up to 92% yield, 94% ee). A representative procedure for this asymmetric Diels-Alder reaction is described below: Sc(OTf)3 (0.02 mmol) and chiral tridentate diphenyl-pybox ligand IV (0.02 mmol) were dissolved in toluene (1.5 mL) and stirred for 30 minutes at room temperature. 2-Arylidene-1,3-indanediones (0.20 mmol) was added to the above-mentioned solution and stirred at 5 ℃ for another 30 minutes. The solution of 2-vinylindoles (0.20 mmol) in toluene (0.5 mL) was then added to the reaction system and the mixture was stirred until the complete consumption of substrates (as monitored by TLC). The reaction mixture was purified directly by flash column chromatography on silica gel (petroleum ether/ethyl acetate=15:1～10:1) to give the corresponding products.

Key words： Diels-Alder reaction; asymmetric synthesis; Lewis acid catalysis; 1,3-indanedione; tetrahydrocarbazole

Cite this article

Tan Fen , Chen Jiarong , Wang Ping , Xiao Wenjing . Asymmetric Diels-Alder Reaction of 2-Arylidene-1,3-indanediones with 2-Vinylindoles Catalyzed by a Sc(OTf)3/Bis(oxazoline) Complex：Enantioselective Synthesis of Tetrahydrocarbazole Spiro Indanedione Derivatives[J]. Acta Chimica Sinica, 2014 , 72(7) : 836 -840 . DOI: 10.6023/A14040237

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