Additive-free thiolysis of epoxides in water: A green and efficient regioselective pathway to β-hydroxy sulfides

Synthetic Communications

Volumn 38, Issue 2, 2008, Pages 282-289

  Abaee, Saeed M ^a   Mojtahedi, Mohammad M ^a   Abbasi, Hassan ^a   Fatemi, Ensieh R ^b  

^a CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Additive free; Aqueous conditions; Epoxides; Green chemistry; Thiolysis

Indexed keywords

1 (4 CHLOROPHENYLTHIO) 3 ISOPROPOXYPROPAN 2 OL; 1 (NAPHTHALEN 2 YLTHIO) 3 PHENOXYPROPAN 2 OL; 1 BUTOXY 3 (4 CHLOROPHENYLTHIO)PROPAN 2 OL; 1 BUTOXY 3 PHENYLTHIOPROPAN 2 OL; 2 (CHLOROMETHYL) OXIRANE; BETA HYDROXY SULFIDE; EPOXIDE; THIOL DERIVATIVE; THIOPHENOL; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 38349143170     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701749963     Document Type: Article

References (37)

1. (a) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003;
2. (b) Yadav, J. S.; Reddy, B. V. S.; Eshwaraiah, B.; Srinivas, M.; Vishnumurthy, P. Three-component coupling reactions in ionic liquids: a facile synthesis of α-aminonitriles. New J. Chem. 2003, 27, 462-465;
3. (c) Kaupp, G. Reactions in supercritical carbon dioxide. Angew. Chem., Int. Ed. Engl. 1994, 33, 1452-1455.
4. (a) Cornils, B.; Hermann, W. A. Aqueous-Phase Organometallic Catalysis; Wiley-VCH: Weinheim, Germany., 1998;
5. (b) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
6. Li, C. J. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem. Rev. 2005, 105, 3095-3166.
7. (a) Luly, J. R.; Yi, N.; Soderquist, J.; Stein, H.; Cohen, J.; Perun, T. J.; Plattner, J. J. New inhibitors of human renin that contain novel Leu-Val replacements. J. Med. Chem. 1987, 30, 1609-1616;
8. (b) Amantini, D.; Fringuelli, F.; Piermatti, O.; Vaccaro, L. Nucleophilic ring opening of 1,2-epoxides in aqueous medium. Arkivoc 2002, 293-311.
9. (a) Corey, E. J.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Samuelsson, B.; Hammarstrom, S. Additions and corrections - Stereospecific total synthesis of a "slow reacting substance" of anaphylaxis leukotriene C-1. J. Am. Chem. Soc. 1980, 102, 3663-3363;
10. (b) Corey, E. J.; Clark, D. A.; Goto, G. Total synthesis of slow reacting substances (SRS): "Leukotriene C-2" (11 trans leukotriene C) (3) and leukotriene D (4). Tetrahedron Lett. 1980, 21, 3143-3146.
11. (a) Hammarstrom, S.; Samuelsson, B.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Corey, E. J. Stereochemistry of leukotriene C-1. Biochem. Biophys. Res. Commum. 1980, 92, 946-953;
12. (b) Corey, E. J.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Samuelsson, B.; Hammarstrom, S. Stereospecific total synthesis of a "slow reacting substance" of anaphylaxis, leukotriene C-1. J. Am. Chem. Soc. 1980, 102, 1436-1439.
13. Kesavan, V.; Bonnet-Delphon, D.; Begue, J. P. Fluoro alcohol as reaction medium: one-pot synthesis of β-hydroxy sulfoxides from epoxides. Tetrahedron Lett. 2000, 40, 2895-2898 and references cited therein.
14. Begue, J. P.; Bonnet-Delphon, D.; Kornilov, A. Synthesis of 3-(alkylthio and phenylthio)-1,1,1-trifluoroalkan-2-ones via ring opening of epoxy ethers. Synthesis 1996, 529-532.
15. (a) Ranu, B. C.; Mandal, T. Indium(I) iodide promoted cleavage of dialkyl disulfides - Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides. Can. J. Chem. 2006, 762-770;
16. 3. Tetrahedron Lett. 2002, 43, 3801-3803;
17. (c) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J. R. Lithium bistrifluoromethanesulfonimidate-mediated regioselective ring opening of aziridines by amines. Synthesis 2002, 2211-2214;
18. (d) Posner, G. H.; Rogers, D. Z. Organic reactions at alumina surfaces: Mild and selective opening of epoxides by alcohols, thiols, benzeneselenol, amines, and acetic acid. J. Am. Chem. Soc. 1977, 99, 8208-8214;
19. (e) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. A highly enantioselective ring opening of epoxides with thiols catalyzed by a gallium·lithium·bis(binaphthoxide) complex. J. Am. Chem. Soc. 1997, 119, 4783-4784;
20. N2 type ring opening of epoxides with thiol. Catal. Commun. 2004, 5, 515-518;
21. 3-catalyzed highly regioselective ring opening of epoxides with thiols. Chem. Lett. 2002, 906-907;
22. (h) Chini, M.; Crotti, P.; Giovani, E.; Macchia, F.; Pineschi, M. Stereo- and regioselective metal salt-promoted ring opening of 1,2-epoxides with thiols in acetonitrile. Synlett 1992, 303-305;
23. (i) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Thiolysis of 1,2-epoxides by thiophenol catalyzed under solvent-free conditions. Tetrahedron Lett. 2003, 44, 6785-6787;
24. (j) Cossy, J.; Bellosta, V.; Hamior, C.; Desmurs, J. R. Regioselective ring opening of epoxides by nucleophiles mediated by lithium bistrifluoromethanesulfonimide. Tetrahedron Lett. 2002, 43, 7083-7086;
25. 40) as a reusable Lewis acid catalyst: Facile regioselective ring opening of epoxides with alcohols, acetic acid and thiols. J. Mol. Catal. A: Chem. 2006, 250, 237-242.
26. 3. Adv. Synth. Catal. 2002, 344, 379-384;
27. 2 as an efficient catalyst in the thiolysis of 1,2-epoxides by thiophenol in aqueous medium. Synlett 2003, 2292-2296;
28. (c) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Easy and environmentally friendly uncatalyzed synthesis of beta-hydroxy arylsulfides by thiolysis of 1,2-epoxides in water. Green Chem. 2003, 5, 436-440;
29. (d) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Zn(II)-catalyzed thiolysis of oxiranes in water under neutral conditions. J. Org. Chem. 2003, 68, 8248-8251;
30. (e) Reddy, M. S.; Srinivas, B.; Srindhar, R.; Narender, M.; Rao, K. R. Highly regioselective thiolysis of oxiranes under supramolecular catalysis involving β-cyclodextrin in water. J. Mol. Catal. A: Chem. 2006, 255, 180-183;
31. 2O: Expeditious approach to beta-amino alcohols and beta-aminothioethers. Green Chem. 2005, 7, 708-710.
32. Pironti, V.; Colonna, S. Microwave-promoted synthesis of beta-hydroxy sulfides and beta-hydroxy sulfoxides in water. Green Chem. 2005, 7, 43-45.
33. (a) Mojtahedi, M. M.; Abbasi, H.; Abaee, M. S.; Mohebali, B. Solvent-free thiolysis of epoxides under lithium perchlorate catalysis. Monatsh. Chem. 2006, 137, 455-458;
34. (b) Mojtahedi, M. M.; Ghasemi, H.; Abaee, M. S.; Bolourtchian, M. Microwave-assisted ring opening of epoxides with thiols on montmorillonite K-10 solid support. Arkivoc 2005, 68-73;
35. 2 catalyzed thiolysis of epoxides under solvent-free conditions. Phosphorus Sulfur Relat. Elem. 2007, 182, 905-910;
36. (d) Mojtahedi, M. M.; Abaee, M. S.; Heravi, M. M.; Behbahani, F. K. Additive-free chemoselective acylation of amines and thiols. Monatsh. Chem. 2007, 138, 95-99.
37. For H-bonded catalyzed reactions, see Schreiner, P. R. Metal-free organocatalysis through explicit hydrogen bonding interactions. Chem. Soc. Rev. 2003, 32, 289-296, and references cited therein.