nitro-Grela

Used Chemicals

• Diethyl Diallylmalonate [D1183]
• nitro-Grela [N1060]
• Dichloromethane

Procedure

In a 200 mL two necked round bottomed flask, nitro-Grela (15 mg, 22 µmol) was added, and purged with N₂. Dichloromethane (40 mL) was charged in the flask, and diethyl diallylmalonate (237 mg, 986 µmol) in dichloromethane (5.5 mL) was added dropwise and the mixture was stirred at room temperature for 6 h. The solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (hexane : EtOAc = 1 : 1) to give diethyl cyclopent-3-ene-1,1-dicarboxylate as a pale yellow oil (206 mg, 98%).

Experimenter's Comments

The reaction mixture was monitored by NMR.

Analytical Data（Diethyl cyclopent-3-ene-1,1-dicarboxylate）

¹H NMR (400 MHz, CDCl₃); δ 5.61 (s, 2H), 4.20 (q, J = 8.0 Hz, 4H), 3.01 (s, 4H), 1.25 (t, J = 8.0 Hz, 6H).

Lead Reference

• Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes:  Enhancement of Catalyst Activity through Electronic Activation
  • A. Michrowska, R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos, K. Grela, J. Am. Chem. Soc. 2004, 126, 9318.

Reference

• Total Synthesis of Mycalolides A and B through Olefin Metathesis
  • M. Kita, H. Oka, A. Usui, T. Ishitsuka, Y. Mogi, H. Watanabe, M. Tsunoda, H. Kigoshi, Angew. Chem. Int. Ed. 2015, 54, 14174.

References

• A Highly Efficient Ruthenium Catalyst for Metathesis Reactions
  • K. Grela, S. Harutyunyan, A. Michrowska, Angew. Chem. Int. Ed. 2002, 41, 4038.
• In an Attempt to Provide a User's Guide to the Galaxy of Benzylidene, Alkoxybenzylidene, and Indenylidene Ruthenium Olefin Metathesis Catalysts
  • M. Bieniek, A. Michrowska, D. L. Usanov, K. Grela, Chem. Euro. J. 2008, 14, 806.

References

• 1)A Highly Efficient Ruthenium Catalyst for Metathesis Reactions
  • K. Grela, S. Harutyunyan, A. Michrowska, Angew. Chem. Int. Ed. 2002, 41, 4038.
• 2)First Diastereoselective Chiral Synthesis of (－)-Securinine
  • T. Honda, H. Namiki, K. Kaneda, H. Mizutani, Org. Lett. 2004, 6, 87.