Efficient catalytic synthesis of optically active cyclic carbonates via coupling reaction of epoxides and carbon dioxide

Tetrahedron Letters

Volumn 48, Issue 2, 2007, Pages 297-300

  Chen, Shu Wei ^a   Kawthekar, Rahul B ^a   Kim, Geon Joong ^a  

^a Inha University   (South Korea)

Author keywords

Chiral cobalt salen; Epoxides; Lewis acid; Resolution

Indexed keywords

CARBON DIOXIDE; CARBONIC ACID DERIVATIVE; EPOXIDE; HALIDE; LEWIS ACID; SODIUM CHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; SYNTHESIS;

EID: 33845221015     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.014     Document Type: Article

References (25)

1. Darensbourg D.J., and Holtcamp M.W. Coord. Chem. Rev. 153 (1996) 155-174
2. Li F., Xia C., Xu L., Sun W., and Chen G. Chem. Commun. (2003) 2042-2043
3. Paddock R.L., and Nguyen S.T. Chem. Commun. (2004) 1622-1623
4. Shaikh A.-A.G., and Sivaram S. Chem. Rev. 96 (1996) 951-976
5. Biggadike K., Angell R.M., Burgess C.M., Farrell R.M., Hancock A.P., Harker A.J., Irving A.J., Irving W.R., Ioannou C.P., Procopiou A., Shaw R.E., Solanke Y.E., Singh O.M.P., Snowden M.A., Stubbs R., Walton S., and Weston H.E. J. Med. Chem. 43 (2000) 19-21
6. Xu X.D., and Moulijin J.A. Energy Fuels 10 (1996) 305 and references cited therein
7. Paddock R.L., and Nguyen S.T. J. Am. Chem. Soc. 123 (2001) 11498-11499
8. Calo V., Nacci A., Monopoli A., and Fanizzi A. Org. Lett. 4 (2002) 2561-2563
9. Yang H., Gu Y., Deng Y., and Shi F. Chem. Commun. (2002) 274-275
10. Yano T., Matsui H., Koike T., Ishiguro H., Fujihara H., Yoshihara M., and Maeshima T. Chem. Commun. (1997) 1129-1130
11. Shen Y.M., Duan W.L., and Shi M. J. Org. Chem. 68 (2003) 1559-1562
12. Lu X.B., Liang B., Zhang Y.J., Tian Y.Z., Wang Y.M., Wang H., and Zhang R. J. Am. Chem. Soc. 126 (2004) 3732-3733
13. Matsumoto K., Fuwa S., and Kitajima H. Tetrahedron Lett. 36 (1995) 6499-6502
14. Shimojo M., Matsumoto K., and Hatanaka M. Tetrahedron. 56 (2000) 9281-9288
15. Shin C.K., Kim S.J., and Kim G.J. Tetrahedron Lett. 45 (2004) 7249-7433
16. Thakur S.S., Li W., Kim S.J., and Kim G.J. Tetrahedron Lett. 46 (2005) 2263-2266
17. Thakur S.S., Li W., Shin C.K., and Kim G.J. Chirality 18 (2006) 37-43
18. Shen and co-workers have reported that only binaphthyldiamino salen-type metal complex was used as catalyst, no reaction occurred. See Ref. 11; R. L. Paddock group also reported that in the absent of co-catalyst yielded only a trace amount of the product. See Refs. 1-3.
19. Ready J.M., and Jacobsen E.N. Angew. Chem., Int. Ed. 41 (2002) 1374-1377
20. White D.E., and Jacobsen E.N. Tetrahedron: Asymmetry 14 (2003) 3633-3638
21. Peng J., and Deng Y. New J. Chem. 25 (2001) 639-641
22. Sun J., Fujita S.I., and Arai M. J. Organomet. Chem. 690 (2005) 3490-3497
23. Kihara N., Hara N., and Endo T. J. Org. Chem. 58 (1993) 6198-6202
24. 3, 400 MHz): δ 1.03 (t, 3H), 1.80 (d, 1H), 4.17 (t, 1H), 4.55 (t, 1H), 4.70 (d, 1H).
25. See Supplementary data for ESIMS and UV anlysis.