Unusual regioselectivity in the opening of epoxides by carboxylic acid enediolates

Molecules

Volumn 13, Issue 6, 2008, Pages 1303-1311

  Domingo, Luis R ^a   Gil, Salvador ^a   Parra, Margarita ^a   Segura, José ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Diastereoselectivity; Lactones; Lithium chloride; Nucleophilic addition; Regioselectivity

Indexed keywords

CARBOXYLIC ACID; EPOXIDE; STYRENE OXIDE;

ARTICLE; CHEMISTRY;

CARBOXYLIC ACIDS; EPOXY COMPOUNDS;

EID: 46749094673     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13061303     Document Type: Article

References (25)

1. See for example: (a) McGarrigle, E.M.; Gilheany, D.G. Chromium- and Manganese-salen Promoted Epoxidation of Alkenes. Chem. Rev. 2005, 105, 1563-1602;
2. (b) Xia, Q.-H.; Ge, H.-Q.; Ye, C.-P.; Liu, Z.-M.; Su, K.-X. Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation. Chem. Rev. 2005, 105, 1603-1662.
3. (a) Izquierdo, J.; López, I.; Rodriguez, S.; González, F. Epoxides as useful synthetic building blocks. Recent Res. Devel. Org. Chem. 2006, 10, 53-61;
4. (b) Gansäuer, A.; Fan, C.-A.; Keller, F.; Karbaum, P. Regiodivergent Epoxide Openings: A Concept in stereoselective Catalysis beyond Classical Kinetic Resolutions and Desymmetrizations. Chem. Eur. J. 2007, 13, 8084-8090;
5. (c) Petragnani, N.; Yonashiro, M. The Reactions of Dianions of Carboxylic Acids and Ester Enolates. Synthesis, 1982, 521-578.
6. Taylor, S. K. Reactions of Epoxides with Ester, Ketone and Amide Enolates. Tetrahedron 2000, 56, 1149-1163.
7. (a) Blicke, F. F.; Wright, P. E. The Reaction of Propylene Oxide, Styrene Oxide, and Cyclohexene Oxide with an Ivanov Reagent. J. Org. Chem. 1960, 25, 693-698;
8. (b) Fujita, T.; Watanabe, S.; Suga, K. Reaction of carboxylic-acids with epoxides using lithium naphthalenide. Australian. J. Chem. 1974, 27, 2205-2218.
9. Movassaghi, M.; Jacobsen, E.N. A Direct Method for the Conversion of Terminal Epoxides into γ-Butanolides. J. Am. Chem. Soc. 2002, 124, 2456-2457.
10. Gil, S.; Torres, M.; Ortúzar, N.; Wincewicz, R.; Parra, M. Efficient Addition of Acid Enediolates to Epoxides. Eur. J. Org. Chem. 2004, 2160-2165.
11. (a) Gil, S.; Parra, M. Dienediolates of carboxylic acids in synthesis. Recent advances. Curr. Org. Chem. 2002, 6, 283-302;
12. (b) Gil, S.; Parra, M. Reactivity control of dianions of carboxylic acids. Synthetic applications. Recent Res. Devel. Org. Chem. 2002, 6, 449-481.
13. Gil, S.; Parra, M.; Rodriguez, P. A simple synthesis of γ-aminoacids. Tetrahedron Lett. 2007, 48, 3451-3453.
14. Parr, R.G.; Yang, W. Density functional-approach to the frontier-electron theory of chemicalreactivity. J. Am. Chem. Soc. 1984, 106, 4049-4050.
15. (a) Becke, A. D. Density-functional thermochemistry .3. the role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652;
16. (b) Lee, C.; Yang, W.; Parr, R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density. Phys. Rev. B 1988, 37, 785-789.
17. Hehre, W.J.; Radom, L.; Schleyer, P.v.R.; Pople, J.A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
18. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J., J. A. ; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02, Frisch, M.J. et al. Gaussian, Inc.: Wallingford CT, 2004.
19. (a) Domingo, L.R.; Gil, S.; Mestres, R.; Picher, M.T. Theoretical Model of Solvated Lithium Dienediolate of 2-Butenoic Acid. Tetrahedron 1995, 51, 7207-7214;
20. (b) Domingo, L.R.; Gil, S.; Mestres, R.; Picher, M.T. Theoretical Model of Solvated Lithium Dienediolate of Methyl Substituted 2-Butenoic Acid. Tetrahedron 1996, 52, 11105-11112.
21. (a) Azizi, N.; Mirmashhori, B.; Saidi, M.R. Lithium perchorate promoted highly regioselective ring opening of epoxides under solvent-free conditions. Catalysis Commun. 2007, 8, 2198-2203;
22. (b) Das, B. Krishnaiah, M., Thirupathi, P., Laxminarayana, K. An efficient catalyst-free regioand stereoselective ring-opening of epoxides with phenoxides using polyethylene glycol as the reaction medium. Tetrahedron Lett. 2007, 48, 4263-4265;
23. (c) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Ring Opening of Epòxides with Sodium Azide in Water. A Regioselective pH-controlled Reaction. J. Org. Chem. 1999, 64, 6094-6096.
24. Sarangi, C.; Das, N.B.; Nanda, B.; Nayak, A.; Sharma, R.P. An Efficient Nucleophilic Cleavage of Oxiranes to 1,2-Azido Alcohols. J. Chem. Res. (S) 1997, 378-379.
25. Myers, A.G.; McKinstry, L. Practical Synthesis of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and their Derivatives. J. Org. Chem. 1996, 61, 2428-2440.