Asymmetric synthesis of Ru(II)-dialkyl-pheox catalysts from (S)-2-Amino-phenylehanol for cyclopropanation
PDF (Vietnamese)

Keywords

Ru(II)-dialkyl-pheox
tổng hợp bất đối xứng
oxazoline
Ru(II)-pheox Ru(II)-dialkyl-pheox
asymmetric synthesis
oxazoline derivatives
Ru(II)-pheox catalyst

How to Cite

1.
Lê TLC, Iwasa S. Asymmetric synthesis of Ru(II)-dialkyl-pheox catalysts from (S)-2-Amino-phenylehanol for cyclopropanation. hueuni-jns [Internet]. 2023Mar.31 [cited 2024May6];132(1A):55-63. Available from: https://jos.hueuni.edu.vn/index.php/hujos-ns/article/view/7056

Abstract

The development of new pharmaceutical products containing pure enantiomers is a recent direction in the world’s pharmaceutical industry. Asymmetric catalysts play an essential role in the synthesis of pure enantiomers. The Ru(II)-pheox catalyst has been reported to be effective for the asymmetric reactions producing pure enantiomers. In this study, an asymmetric synthesis of Ru(II)-dialkyl-pheox derivatives is proposed. The process consists of the asymmetric synthesis of oxazoline derivatives from precursors and the complexation between ruthenium and oxazoline ligands. With this procedure, four Ru(II)-dialkyl-pheox derivatives were successfully synthesized with a high yield (>60%).

https://doi.org/10.26459/hueunijns.v132i1A.7056
PDF (Vietnamese)

References

  1. Hava C, Efrat G, Liron L, Israel A, “Trends in the development of chiral drugs”. Drug Discovery Today. 2004;3:105-110.
  2. Hussein AY, Wei S, Nazir A, Si C, Francis V. Ruthenium Pincer Complexes: Synthesis and Catalytic Applications. Advanced Synthesis and Catalysis. 2015;357:283-330.
  3. Sparr C, Schweizer WB, Senn, HM, Gilmour, R. Fluorinated Quinine Alkaloids: Synthesis, X-ray Structure Analysis and Anti¬malarial Parasite Chemotherapy. Angewandte International Edition Chemie. 2009;48:3065-3068.
  4. Daniela I, Daniela MC and Emma G. The ligand influence in stereoselective carbene transfer reactions promoted by chiral metal porphyrin catalysts. Dalton Transactions. 2016;45:15746-15761.
  5. Chi LTL, Agus S, Da LH, Soda C, Kazutaka S, Iwasa S. Catalytic Asymmetric Intermolecular Cyclopropanation of a Ketone Carbene Precursor by a Ruthenium(II)‐Pheox Complex. Advanced Synthesis and Catalysis. 2018;361(5):951-955.
  6. Yoko N, Soda C, Kazutaka S, Iwasa S. Ru(II)−Pheox Catalyzed Asymmetric Intramolecular Cyclopropanation of Electron-Deficient Olefins. Organic Letters. 2015;17(11): 2792-2795.
  7. Otsuki T, Kumagai J, Kohari Y, Okuyama Y, Kwon E, Seki C, et al. Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β- Unsaturated Aldehydes. European Journal of Organic Chemistry. 2015;33:7292-7300.
  8. Tse MK, Bhor S, Klawonn M, Anilkumar G, Jiao H, Döbler C, et al. Ruthenium-Catalyzed Asymmetric Epoxidation of Olefins Using H2O2, Part I: Synthesis of New Chiral N,N,N-Tridentate Pybox and Pyboxazine Ligands and Their Ruthenium Complexes. Chemistry – A European Journal. 2006; 12(7):1855-74.
  9. Raphael MP, Jurgen G, Odile E, Michele C. The Grignard Reaction – Unraveling a Chemical Puzzle. Journal of the American Chemical Society. 2020; 142(6),2984-2994.
  10. Robert JO, David R. Organic Chemistry Study Guide. Elsevier. 2015;21,385-418.
  11. María CM, Liliana RO. Microwave-Assisted Synthesis of 2‑Aryl-2-oxazolines, 5,6-Dihydro‑4H‑1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines. Organic Letters. 2016; 18,6116-6119.
  12. Chanthamath S, Iwasa S. Enantioselective Cyclopropanation of a Wide Variety of Olefins Catalyzed by Ru(II)–Pheox Complexes. Accounts of Chemical Research. 2016;49(10):2080-90.
  13. Anil KS, Deepak KD, Koushlesh M, Saraswati PM, Rajni Y, Pankaj K. Properties and Applications of Ruthenium. In: Mohindar Singh S, Alan DB, editors. Noble and Precious Metals. Rijeka: IntechOpen; 2018. p. Ch. 17.
  14. Motswainyana WM, Ajibade PA. Anticancer Activities of Mononuclear Ruthenium(II) Coordination Complexes. Advances in Chemistry. 2015;2015:859730.
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