Synthesis of β-hydroxy sulfones via opening of hydrophilic epoxides with zinc sulfinates in aqueous media

Tetrahedron

Volumn 62, Issue 18, 2006, Pages 4540-4548

  Chumachenko, Nataliya ^a   Sampson, Paul ^a  

^a KENT STATE UNIVERSITY   (United States)

Author keywords

Hydroxy sulfone; Butadiene sulfone; Butadienyl sulfones; Epoxide; Zinc sulfinate

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 2 (METHYLSULFONYL)ETHANOL; ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; BENZENE DERIVATIVE; EPOXIDE; ETHYLENE OXIDE; FUNCTIONAL GROUP; ORGANIC SOLVENT; PROPYLENE OXIDE; REAGENT; SULFONE DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE; ZINC OXIDE;

AQUEOUS SOLUTION; ARTICLE; HYDROPHILICITY; METHODOLOGY; MICHAEL ADDITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33646103693     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.043     Document Type: Article

References (42)

1. Polunin E.V., Zaks I.M., Moiseenkov A.M., and Semenovskii A.V. Izv. Akad. Nauk SSSR, Ser. Khim. 3 (1979) 641-643
2. Krug R.C., Rigney J.A., and Tichelaar G.R. J. Org. Chem. 27 (1962) 1305-1309
3. Chabardes, P.; Julia, M.; Menet, A. Ger. Offen 2,319,518, 1973; U.S. Patent 3,890,393, 1975; Chem. Abstr. 1974, 80, 27403x.
4. Burger J.J., Chen T.B.R.A., De Waard E.R., and Huisman H.O. Tetrahedron 36 (1980) 723-726
5. Naf F., Decorzant R., and Escher S.D. Tetrahedron Lett. 23 (1982) 5043-5046
6. Solladie, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, pp 133-170; and references cited therin.
7. Crandall J.K., and Pradat C. J. Org. Chem. 50 (1985) 1327-1329 and references cited therein
8. Culvenor C.C.J., Davies W., and Heath N.S. J. Chem. Soc. (1949) 278-282
9. Culvenor C.C.J., Davies W., and Savige W.E. J. Chem. Soc. (1949) 2198-2206
10. Still I.W.J., and Ablenas F.J. Synth. Commun. 12 (1982) 1103-1110
11. Biswas G.K., and Bhattacharyya P. Synth. Commun. 21 (1991) 569-573
12. Maiti A.K., and Bhattacharyya P. Tetrahedron 50 (1994) 10483-10490
13. Zhu S.Z., Qin C.Y., and Xu B. Phosphorus, Sulfur, Silicon Relat. Elem. 113 (1996) 259-262
14. Brace N.O. J. Fluorine Chem. 102 (2000) 21-41
15. 2Na, 1 equiv) reacts with cyclohexene oxide (1 equiv) in ethanol-water (1/1) to give the corresponding β-hydroxy sulfone product, albeit with low (27%) conversion.
16. (a) Chumachenko, N.; Sampson, P. Abstracts of Papers, 28th ACS National Meeting, Philadelphia, PA, Aug 22-26, 2004; ORGN 621.
17. Chumachenko N., Sampson P., Hunter A.D., and Zeller M. Org. Lett. 7 (2005) 3203-3206
18. Crumbie R.L., and Ridley D.D. Aust. J. Chem. 34 (1981) 1017-1026
19. 18
20. Polunin E.V., Kharchevnikov A.P., and Kashin A.N. Zh. Org. Khim. 31 (1995) 775-778
21. 4 employed the same potassium salt in reaction with five more allylic halides (38-97% yield), benzyl halide (81% yield) and methyl halide (29% yield) in DMSO at rt.
22. 11 used a 1.5/1 ratio of p-toluenesulfinate/epoxide in their studies, presumably to avoid problems associated with the rapid hydrolysis of the epoxide during the latter stages of their reactions (pH 14). Since we needed to employ valuable sulfinate salts and inexpensive epoxides in future studies, we employed a 1/1.37 ratio of sulfinate/epoxide. This also allowed direct comparison with our studies using Zn sulfinates (see Section 2).
23. Konieczny M.T., Horowska B., Kunikowski A., Konopa J., Wierzba K., Yamada Y., and Asao T. Synthesis (2001) 1363-1367
24. Hanefeld W., and Landwehr J. Pharmazie 50 (1995) 344-351
25. Whitmore F.C., Hamilton F.H., and Thurman N. J. Am. Chem. Soc. 45 (1923) 1066-1068
26. Mase N., Watanabe Y., Ueno Y., and Toru T. J. Org. Chem. 62 (1997) 7794-7800
27. Cookson P.G., and Deacon G.B. Aust. J. Chem. 24 (1971) 1599-1610
28. Bazlen M. Chem. Ber. 60 (1927) 1470-1479
29. Interestingly, Zn methanesulfinate and Zn butanesulfinate did not precipitate from the reaction mixture unless water was added. They were isolated as the corresponding dihydrates 9a and 9b. In contrast, Zn phenylmethanesulfinate and Zn p-toluenesulfinate precipitated directly from the ethanol solution. The precipitates contained some solvating ethanol, which was substituted by water on drying in air to produce the corresponding dihydrates 9c and 9d.
30. For example, 2-(methylsulfonyl)ethanol (10) is used in the synthesis of urethane-protected amines and amino acids (a). Greene T.W., and Wuts P.G. Protective Groups in Organic Synthesis. 3rd ed. (1999), Wiley, New York p 540
31. Henklein P., Heyne H.-U., Halatsch W.-R., and Niedrich H. Synthesis (1987) 166-167
32. Tamura N., Natsugari H., Kawano Y., Matsushita Y., Yoshioka K., and Ochiai M. Chem. Pharm. Bull. 35 (1987) 996-1015 protected phosphate esters
33. (d). Bradshaw B., Dinsmore A., Ajana W., Collison D., Garner C.D., and Joule J.A. J. Chem. Soc., Perkin Trans. 1 (2001) 3239-3244 and protected phenols
34. (e). Rogers J.F., and Green D.M. Tetrahedron Lett. 43 (2002) 3585-3587
35. Out of all observed byproducts (12a-d and 13a-d), only 2-(methylsulfonyl)propan-1-ol (12a) has been previously described in the literature:. Alcudia F., Brunet E.R., Garcia Ruano J.L., Rodriguez J.H., and Sanchez F. J. Chem. Res., Miniprint (1982) 2826-2850
36. 13C NMR spectrum of the reaction mixture at 66.0/66.2 and 70.40/70.46 ppm. By comparison with the sulfinate esters 13a-c obtained earlier, we tentatively attribute these signals to the C1 and C2 carbons of the 2-hydroxypropyl fragments in the two diastereomers of 13d.
37. 1H NMR spectrum of 18a.
38. 5 (2.3, 1.7 Hz).
39. Haynes R.K., and Schober P.A. Aust. J. Chem. 40 (1987) 1249-1265
40. Alcudia F., Garcia Ruano J.L., Rodriguez J., and Sanchez F. Can. J. Chem. 57 (1979) 2426-2433
41. Kader A.T., and Stirling C.J.M. J. Chem. Soc. (1962) 3686-3692
42. (b) (S)-(+) enantiomer:. Kozikowski A.P., Mugrage B.B., Li C.S., and Felder L. Tetrahedron Lett. 27 (1986) 4817-4820