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Acta Chimica Sinica >

2016 , Vol. 74 >Issue 10: 800 - 804

DOI: https://doi.org/10.6023/A16070358

Article

Highly Enantioselective Intermolecular Rauhut–Currier Reaction of Activated Alkenes Catalyzed by Multifunctional Chiral Phosphine

  • Zhou Wei ,
  • Gao Lihua ,
  • Tao Mengna ,
  • Su Xiao ,
  • Zhao Qingjie ,
  • Zhang Junliang
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  • a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
    b Jilin Dongfeng Veterinary Pharmacy Factory, Jilin 132011;
    c Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433

Received date: 2016-07-23

  Online published: 2016-09-06

Supported by

Project supported by the "973" Programs (No. 2015CB856600), the National Natural Science Foundation of China (Nos. 21372084, 21425205), and the Changjiang Scholars and Innovative Research Team in University (PCSIRT).

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Abstract

The Rauhut-Currier (R-C) reaction, first disclosed by Rauhut and Currier in 1963, is an atom economy strategy for the construction of carbon-carbon bond and a wide range of synthetic valuable building blocks. During the past few decades, significant progress on the enantioselective intramolecular R-C reactions has been achieved by utilizing diverse chiral nucleophilic catalysts such as cysteine derivatives, L-prolinol, hydrogen-bonding catalyst and β-aminephosphine. However, compared to the well-developed enantioselective intramolecular R-C reactions, the enantioselective cross intermolecular R-C reaction concerning two different alkenes has been rarely explored so far. The enantioselective cross R-C reaction still suffers from a series of drawbacks such as low reactivity, enantioselectivity, limited substrate scope and higher catalyst loading. Thus, the development of novel chiral nucleophilic catalyst, for highly enantioselective cross R-C reaction is highly desirable. In this article, we wish to report the application of Xiao-Phos in the highly enantioselective cross intermolecular R-C reaction of vinyl ketone and activated alkenes. Accordingly, a stirred solution of 3-aroyl acrylates 1 (0.2 mmol) and (S,RS)-X8 (0.02 mmol) in toluene (2 mL) was cooled to -20℃. Subsequently, vinyl ketone 2 (0.4 mmol for aryl vinyl ketone and 0.6 mmol for alkyl vinyl ketone) was added in one portion through a syringe. The mixture was stirred at this temperature until completion of 3-aroyl acrylate as indicated by TLC. After completion of the reaction, the reaction mixture was directly purified by silica gel chromatography to afford the desired RC product. What’s more, control experiments demonstrated that the presence of free sulfinamide N-H in Xiao-Phos is crucial for the enantioselective cross R-C reaction. Finally, for more details about (S,RS)-X8 in the enantioselective cross R-C reaction, control experiments monitored by 31P NMR spectroscopy were conducted and the 31P NMR experiments indicated that this cross intermolecular R-C reaction was initiated by the Michael addition of (S,RS)-X8 to vinyl ketone 2.

Key words： chiral phosphine catalysis; Rauhut-Currier reaction; 3-aroyl acrylates; vinyl ketones; nucleophilic catalysis

Cite this article

Zhou Wei , Gao Lihua , Tao Mengna , Su Xiao , Zhao Qingjie , Zhang Junliang . Highly Enantioselective Intermolecular Rauhut–Currier Reaction of Activated Alkenes Catalyzed by Multifunctional Chiral Phosphine[J]. Acta Chimica Sinica, 2016 , 74(10) : 800 -804 . DOI: 10.6023/A16070358

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