Science Citation Index Related Paper:

Enantioselective Catalytic Ring Opening of Epoxides with Carboxylic Acids
Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776.
Description: The mechanism in this paper utilizes carboxylic acids as inexpensive and effective nucleophiles in the salen(Co)-catalyzed ring opening reactions of epoxides which yield monoesters. It was found that it was most advantageous to add carboxylic acid to the epoxide-Co(III) catalyst complex under aerobic conditions (in the presence of molecular oxygen) prior to addition of the diisopropylethylamine, since the amine was capable of inhibiting the complex. The mechanism discussed in this paper is similar to our mechanism because it involves a divalent oxygen nucleophile in an epoxide ring opening, with proton transfer mediated by a trivalent amine base.  In the mechanism for this paper specifically, the diisopropylethylamine base deprotonates the carboxylic acid to activate the carboxylate nucleophile and then re-protonates the original epoxide oxygen in a final workup step.

Three Papers Citing Related Paper:

1) Efficient Ring Opening Reaction of Epoxides with Oxygen Nucleophiles Catalyzed by Quaternary Onium Salt
Kim, J. W.; Cho, D. W.; Park, G.; Kim, S. H.; Ra, C. S. Bull. Korean Chem. Soc. 2013, 34, 2286-2290.
Description: This mechanism is similar to the mechanism in the commonly cited paper in that it involves oxygen nucleophile carboxylate which attacks the less-substituted carbon of the epoxide, resulting in opening of the ring. Proton transfer is mediated by a base catalyst, such as an ammonium or phosphonium salt.

 

2) Tetrabutylammonium bromide-mediated ring opening reaction of N-tosylaziridines with carboxylic acids in DMF
Li, X.; Li, G.; Chang, H.; Zhang, Y.; Wei, W. RSC Adv. 2014, 4, 6490-6495.
Description: Reactivity similar to epoxides is demonstrated in aziridines, which are three-membered, nitrogen-containing, highly strained rings that react efficiently with a variety of nucleophiles. With tetrabutylammonium bromide (TBAB) as the base catalyst, the study demonstrated that ring opening of N-tosylcyclohexylaziridine with 4-nitrobenzoic acid (carboxylate nucleophile) was most effective when done in the presence of dimethylformamide (DMF).

3) Catalytic Activity of Schiff Base Cobalt(III) Complexes Immobilized on Terpolymers of Glycidyl Methacrylate in the Addition of Carboxylic Acids to Terminal Epoxides
Bukowska, A.; Bukowski, W.; Noworól, J. J. Appl. Polym. Sci. 2010, 117, 655-663.
Description: In this reaction, amide nitrogen acts both as the epoxide ring opening nucleophile as well as the proton donor in a workup step that results in protonation of the oxyanion from the epoxide opening. This mechanism is similar to the original with the slight modification of having the same molecule (nitrogen nucleophile and amide proton donor) perform two distinct functions necessary for epoxide opening.

Website-Wide References:

1. Shi, J.; Manolikakes, G.; Yeh, C.-H.; Guerrero, C. A.; Shenvi, R. A.; Shigehisa, H.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 8014-8027.
2. Harvard University: The Evans Group. PKa’s of Inorganic and Oxo-Acids. http://www2.lsdiv.harvard.edu/labs/evans/pdf/evans_pKa_table.pdf (accessed Apr 1, 2014).
3. University of Wisconsin: The Organic Chemistry Undergraduate Laboratories. Refluxing. http://www.chem.wisc.edu/areas/organic/orglab/tech/reflux.htm (accessed Apr 1, 2014).
4. Paddock, R. L.; Hiyama, Y.; McKay, J. M.; Nguyen, S. T. Tetradhedron Lett. 2004, 45, 2023-2026.
5. Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776.
6. Kim, J. W.; Cho, D. W.; Park, G.; Kim, S. H.; Ra, C. S. Bull. Korean Chem. Soc. 2013, 34, 2286-2290.
7. Li, X.; Li, G.; Chang, H.; Zhang, Y.; Wei, W. RSC Adv. 2014, 4, 6490-6495.
8. Bukowska, A.; Bukowski, W.; Noworól, J. J. Appl. Polym. Sci. 2010, 117, 655-663.