Acid-promoted thioacetalization in water using 2-(1,3-dithian-2-ylidene) malonic acid as an odorless and efficient thioacetalization reagent

Synthetic Communications

Volumn 37, Issue 6, 2007, Pages 993-1000

  Ouyang, Yan ^a   Dong, Dewen ^a   Liang, Yongjiu ^a   Chai, Yanyan ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

2 (1,3 dithian 2 ylidene)malonic acid; Chemoselectivity; p dodecylbenzenesulfonic acid; Thioacetalization; Water

Indexed keywords

2 (1,3 DITHIAN 2 YLIDENE)MALONIC ACID; ACETAL DERIVATIVE; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; MALONIC ACID DERIVATIVE; REAGENT; SULFONIC ACID DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ACETALIZATION; ARTICLE; CATALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; THIN LAYER CHROMATOGRAPHY; THIOACETALIZATION;

EID: 33847304930     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910601163984     Document Type: Article

References (35)

1. (a) Breslow, R.; Rideout, D. C. Hydrophobic acceleration of Diels-Alder reactions. J. Am. Chem. Soc. 1980, 102, 7816-7817;
2. (b) Breslow, R. Hydrophobic effects on simple organic reactions in water. Acc. Chem. Res. 1991, 24, 159-164;
3. (c) Breslow, R. Determining the geometries of transition states by use of antihydrophobic additives in water. Acc. Chem. Res. 2004, 37, 471-478.
4. (a) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Catalysis: Concepts and Applications; Wiley-VCH: Weinheim, 1998;
5. (b) Grieco, P. A. Organic Synthesis in Water; Thomson Science: Glawsgow, Scotland, 1998;
6. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997;
7. (d) Kobayashi, S.; Manabe, K.; Shibasaki, M.; Stoddart, J. F.; Vogtle, F. In Stimulating Concepts in Chemistry; Wiley-VCH: Weinheim, 2000.
8. (a) Li, C.-J.; Chan, T.-H. Organic syntheses using indium-mediated and catalyzed reactions in aqueous media. Tetrahedron 1999, 55, 11149-11176;
9. (b) Li, C.-J. Organic reactions in aqueous media with a focus on carbon-carbon bond formation. Chem. Rev. 1993, 93, 2023;
10. (c) Li, C.-J. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update. Chem. Rev. 2005, 105, 3095-3165;
11. (d) Kobayashi, S.; Manabe, K. Development of novel Lewis acid catalysts for selective organic reactions in aqueous media. Acc. Chem. Res. 2002, 35, 209-217.
12. (a) Iimura, S.; Manabe, K.; Kobayashi, S. Hydrophobic polymer-supported catalyst for organic reactions in water: Acid-catalyzed hydrolysis of thioesters and transprotection of thiols. Org. Lett. 2003, 5 (2), 101-103;
13. (b) Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. Dehydration reactions in water. Brøsnsted acid-surfactant combined catalyst for ester, ether, thioether, and dithioacetal formation in water. J. Am. Chem. Soc. 2002, 124, 11971-11978.
14. (a) Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994;
15. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999.
16. (a) Breit, B. Dithioacetals as an entry to titanium-alkylidene chemistry: A new and efficient carbonyl olefination. Angew. Chem. Int. Ed. 1998, 37 (4), 453-456;
17. N2′ manifolds. J. Am. Chem. Soc. 2002, 124, 14516-14517.
18. (a) Page, P. C. B.; Prodger, J. C.; Westwood, D. Diastereoselectivity in the addition of Grignard reagents to ketones controlled by the 1,3-dithiane 1-oxide asymmetric building block. Tetrahedron 1993, 49, 10355-10368;
19. (b) Tani, H.; Masumoto, K.; Inamasu, T.; Suzuki, H. Tellurium tetrachloride as a mild and efficient catalyst for dithioacetalization. Tetrahedron Lett. 1991, 32, 2039-2042;
20. (c) Tietze, L. F.; Weigand, B.; Wulff, C. A mild and efficient method for the preparation of 1,3-dithianes from aldehydes and ketones. Synthesis 2000, 69-71.
21. (a) Garlaschelli, L.; Vidari, G. Anhydrous lanthanum trichloride, a mild and convenient reagent for thioacetalization. Tetrahedron Lett. 1990, 31, 5815-5186;
22. (b) Kumar, P.; Reddy, R. S.; Singh, A. P.; Pandey, B. H-Y zeolite: An efficient catalyst for thioacetalization. Tetrahedron Lett. 1992, 33, 825-826;
23. (c) Saraswathy, V. G.; Sankararaman, S. Chemoselective protection of aldehydes as dithioacetals in lithium perchlorate-diethyl ether medium: Evidence for the formation of oxocarbenium ion intermediate from acetals. J. Org. Chem. 1994, 59, 4665-4670;
24. 2. Synlett 1999, 415-416;
25. (e) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. Iodine catalyzes efficient and chemoselective thioacetalization of carbonyl functions, transthioacetalization of O,O- and S,O-acetals and acylals. J. Org. Chem. 2001, 66, 7527-7529;
26. (f) Muthusamy, S.; Babu, S. A.; Gunanathan, C. Indium(III) chloride as an efficient, convenient catalyst for thioacetalization and its chemoselectivity. Tetrahedron Lett. 2001, 42, 359-362;
27. (g) Kamal, A.; Chouhan, G. Scandium triflate as a recyclable catalyst for chemoselective thioacetalization. Tetrahedron Lett. 2002, 43, 1347-1350;
28. (h) Kamal, A.; Chouhan, G. Chemoselective thioacetalization and transthioacetalization of carbonyl compounds catalyzed by immobilized scandium(III) triflate in ionic liquids. Tetrahedron Lett. 2003, 44, 3337-3340.
29. (a) Liu, Q.; Che, G.; Yu, H.; Liu, Y.; Zhang, J.; Zhang, Q.; Dong, D. The first non-thiolic, odorless 1,3-propanedithiol equivalent and its application in thioacetalization. J. Org. Chem. 2003, 68, 9148-9150;
30. (b) Yu, H.; Liu, Q.; Yin, Y.; Fang, Q.; Zhang, J.; Dong, D. α,α-Diacetyl cyclic ketene dithioacetals: Odorless and efficient dithiol equivalents in thioacetalization reactions. Synlett 2004, 999-1002;
31. (c) Liu, J.; Liu, Q.; Yu, H.; Ouyang, Y.; Dong, D. Odorless thioacetalization reagent 2-[1,3]dithian-2-ylidene-3-oxo-butanamide and its chemoselectivity. Synth. Commun. 2004, 34 (24), 4545-4556.
32. Dong, D.; Ouyang, Y.; Yu, H.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. Chemoselective thioacetalization in water: 3-(1,3-Dithian-2-ylidene)pentane-2,4- dione as an odorless, efficient and practical thioacetalization reagent. J. Org. Chem. 2005, 70, 4535-4537.
33. (a) Choi, E. B.; Youn, I. K.; Pak, C. S. Preparation of protected β-keto aldehydes from β-keto ester via selective reduction of acyl(alkoxycarbonyl)ketene dithioacetals. Synthesis 1988, 792-794;
34. (b) Mellor, J. M.; Schofield, S. R.; Korn, S. R. Routes to building blocks for heterocyclic synthesis by reduction of ketene dithioacetals. Tetrahedron 1997, 53 (50), 17151-17162.
35. Zhao, Y.; Liu, Q.; Sun, R.; Zhang, Q.; Xu, X. Iododecarboxylation reactions of α-oxo ketene dithioacetals: The new route to α-iodo ketene dithioacetals. Synth. Commun. 2004, 34 (3), 463-469.