A scope of chiral cyclopropane of diazo acetoxy acetone with styrene derivatives, diazo acetoxy acetone derivatives with styrene catalyzed by p-nitro- Ru(ii)-diphenyl-Pheox
Vol. 132 No. 1C (2023), Original Article
Vol. 132 No. 1C (2023)

A scope of chiral cyclopropane of diazo acetoxy acetone with styrene derivatives, diazo acetoxy acetone derivatives with styrene catalyzed by p-nitro- Ru(ii)-diphenyl-Pheox

Original Article
https://doi.org/10.26459/hueunijns.v132i1C.7126
Published 2023-09-30
Le Thi Loan Chi*
University of Medicine and Pharmacy, Hue University, 6 Ngo Quyen St., Hue, Vietnam
Seiji Iwasa
Toyohashi University of Technology, Toyohashi, Aichi, Japan
PDF (Vietnamese)

Keywords

p-nitro-Ru(II)-diphenyl-Pheox
tổng hợp bất đối xứng
diazo ketone
phản ứng tạo sản phẩm đối quang cyclopropan
Ru(II)-Pheox p-nitro-Ru(II)-diphenyl-Pheox
asymmetric chemistry
Ru(II)-Pheox catalysts
diazo ketones
asymmetric cyclopropanation

How to Cite

1.
Lê TLC, Iwasa S. A scope of chiral cyclopropane of diazo acetoxy acetone with styrene derivatives, diazo acetoxy acetone derivatives with styrene catalyzed by p-nitro- Ru(ii)-diphenyl-Pheox . hueuni-jns [Internet]. 2023Sep.30 [cited 2024Dec.22];132(1C):99-113. Available from: https://jos.hueuni.edu.vn/index.php/hujos-ns/article/view/7126
ACM ACS APA ABNT Chicago Harvard IEEE MLA Turabian Vancouver

Download Citation

Endnote/Zotero/Mendeley (RIS) BibTeX
Crossref
Scopus
Google Scholar
Europe PMC

Abstract

In the publication about "The optimization on catalytic asymmetric intermolecular cyclopropanation of diazo acetoxy acetone and styrene by using p-nitro-Ru(II)-diphenyl-Pheox complex”, we presented the asymmetric cyclopropanation of diazo acetoxy acetone and styrene catalyzed by the asymmetric complex p-nitro-Ru-diphenyl-Pheox. This procedure has also been optimized under suitable solvent and temperature conditions and the products were achieved with high yields, excellent diastereoselectivity >99:1, and high enantioselectivity up to 95%. It is the first published result, demonstrating the effectiveness of this catalyst in the production of cyclopropane enantiomers. Additionally, this study provides sufficient evidence on how cyclopropane enantiomers are formed and how preferential trans products are formed. We continue to expand our research in order to further verify the published mechanism as well as expand the substrates that can be used to create highly selective cyclopropane enantiomers. Using p-nitro-Ru(II)-diphenyl-Pheox as a catalyzer. We investigated the reaction between diazo acetoxy acetone and styrene derivatives, as well as the reaction between diazo acetoxy acetone derivatives with styrene, the obtained products have high stereoselectivity (up to 99:1), with good yield (up to 92%), excellent enantioselectivity (up to 98% ee). This first published study contributes to the availability of many new and useful enriched cyclopropyl ketone products, found in natural and synthetic products of medicinal significance.

https://doi.org/10.26459/hueunijns.v132i1C.7126
PDF (Vietnamese)

References

  1. Lebel H, Marcoux JF, Molinaro C, Charette ABJ, Stereoselcevtive cyclopropanation reactions. Chemical Review. 2003;103:977-1050.
  2. Thibodeaux CJ, Chang WC, Liu HW. The enzymatic chemistry of cyclopropane, epoxide, and azỉidine biosynthesis. Chemical Review. 2012;112:1681-1709.
  3. Gagnon A, Duplessis M; Fader L. Organic Preparation and Procedures International. Arylcyclopropanes: Properties, synthesis and use in medical chemistry. 2010;42:1-69.
  4. Beaulieu L PB, Zimmer LE, Gagnon A, Cherette AB. Highly enantioselective synthesis of 1,2,3-substituted cyclopropanes by using α-Iodo- and α-chloromethylzinc carbenoids. Chemistry (Weinheim An Der Bergstrasse, Germany). 2012;18:14784-14791.
  5. Bartoli G, Bencivenni G, Dalpozzo R. Asymmetric cyclopropanation reactions. Synthesis Review. 2014; 46:979-1029.
  6. Alliot J, Gravel E, Pillon F, Buisson DA, Nicolas M, Doris E. Enantioselective synthesis of levomilnacipran. Chemical Commununication. 2012;48:8111-8113.
  7. Anthes R, Benoit S, Chen CK, Corbett EA, Corbett R M, DelMonte AJm Gingras S, et al. An improved synthesis of a selective seretonin reuptake inhibitor. Organic process Research & Development. 2008;12: 178-182.
  8. Chawner SJ, Cases-Thomas MJ, Bull JA. Divergent synthesis of cyclopropane-containing lead-like compounds, fragments and building blocks through a cobalt catalyzed cyclopropanation of phenyl vinyl sulfide. European Journal of Organic Chemistry. 2017;34:5015-2024.
  9. Chanthama S, Ozaki S, Shibatomi K, Iwasa S. Highly stereoselective synthesis of cyclopropylphosphonates catalyzed by chiral Ru(II)-Pheox complex. Organic Letter. 2014;16:3012 -3015.
  10. Reest JVD, Gottlieb E. Anti-cancer effects of vitamin C revisted. Cell Research. 2016; 26:269-270.
  11. Xu H, Lybrand D, Bennewitz S, Tissier A, Last RL, Pichersky E. Production of trans-chrysanthemic acid, the monoterpene acid moiety of natural pyrethrin insecticides, in tomato fruit. Metabolic Engineering. 2018;47:271-278.
  12. Palko JW, Buist PH, Manthorpe JM. A flexible and modular stereoselective synthesis of (9R,10S)-dihydrosterculic acid. Tetrahedron: Asymmetric. 2013;24:165-168.
  13. Nozaki H, Takaya H, Moriuti S, Noyori R. Homogeneous catalysis in the decomposition of diazo coumpounds by copper chelates: Asymmetric carbenoid reactions. Tetrahedron. 1968;24,3655-3669.
  14. DeAngelis A, Dmitrenko O, Yap GPA, Fox JM. Chiral crown conformation of Rh2(S-PTTL)4: Enantioselectivive cyclopropanation with -alkyl--diazoesters. Journal of The American Chemical Society. 2009;131:7230-7231.
  15. Ralph WA, Liam B, Péter K, Mohammadali F, Liladhar P, Mathias N, et al. Diastereomeric ratio determination by high sensitivity band-selective pure shift NMR spectroscopy. Chemical Communications. 2014;50:2512-2514.
  16. Robert E, Gawley. Do the Terms "% ee" and "% de" Make Sense as Expressions of Stereoisomer Composition or Stereoselectivity? The Journal of Organic Chemistry. 2006;71(6):2411-2416.
  17. Chen R, Zhao Y, Su H, Shao Y, Xu Y, Ma M, et al. In situ generation of quinolinium ylides from diazo compounds: Copper-catalyzed of indolizine. Journal of Organic Chemistry. 2017;82:9291-9304.
  18. Xia Z, Hu J, Gao YQ, Yao Q, Xie, W. Facile access to 2,2-disubstituted indolin-3-ones via a cascade Fischer indolization/Claisen rearrangement reaction. Chemical Communications. 2017;53:7485-7488.
  19. Pace V, Verniest G, Sinisterra JV, Alcántara AR, Kimpe ND. Improved Arndt-Eistert synthesis of -diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger. Journal of Organic Chemistry. 2010;76:5760-5763.
  20. Stevens C.L, Sherr AE. The chloro--diphenylacetones. Preparation, proof of structure, and reactions with base. Journal of Organic Chemistry. 1952;17:1228-1234.
  21. Lngvik O, Saloranta T, Kirilin A, Liljeblad A, Mki-Arvela P, Kanerva LT, et al. Dynamic kinetic resolution of rac-2-hydroxy-1-indanone by using a heterogeneous Ru(OH)3/Al2O3 recamization catalyst and lipase. ChemCatChem, 2010;2:1615-1621.
  22. Ogawa K, Terada T, Muranaka Y, Hamakawa T, Hashimoto S, Fujii S. Chemical and Pharmaceutical Bulletin. 1986; 34:3252-3266.
  23. Hayashi D, Igura Y, Masui Y, Onaka M. Stabilization and activation of unstable propynal in the zeolite nanospace and its application to addition reactions. Catalysis Science & Technology. 2017;7:4422-4430.
  24. (a) Nicolas I, Maux PL, Simonneaux G. Intermolecular asymmetric cyclopropanation with diazoketones catalyzed by chiral ruthenium porphyrins. Tetrahedron Lett. 2008;49:2111-2113. (b) Nicolas I, Roisnel T, Maux PL, Simonneaux G. Asymmetric intermolecular cyclopropanation of alkenes by diazoketones catalyzed by Halterman iron. Tetrahedron Lett. 2009; 50:5149-5151.
  25. 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. 2019;361(5):951-955.
  26. Bauta W, Dodd J, Bullington J, Gauthier D, Leo G, McDonnell P. Stereoselectivity in the rhodium(II) acetate catalysed cyclopropantions of 2-diazo-1-indanone with styrenes. Tetrahedron Letters. 2000;41:1491-1494.
Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Copyright (c) 2023 Array