Catalytic asymmetric addition of carbon dioxide to propylene oxide with unprecedented enantioselectivity

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4401-4404

  Berkessel, Albrecht ^a   Brandenburg, Marc ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; EPOXIDE; PROPYLENE OXIDE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

CARBON DIOXIDE; CATALYSIS; EPOXY COMPOUNDS; STEREOISOMERISM;

EID: 33750069752     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061501d     Document Type: Article

References (37)

1. (a) Collins, A. N.; Sheldrake, G. N. Chirality in Industry II; Crosby, J., Ed.; Wiley: New York, 1996.
2. (b) Song, C. E.; Lee, S.-G. Chem. Rev. 1996, 102, 3495.
3. (c) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885.
4. (a) Katsuki, T. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 621.
5. (b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 649.
6. (c) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, Germany, 2005; pp 277-287.
7. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
8. (a) Shaikh, A. A. G.; Sivaram, S. Chem. Rev. 1996, 96, 951.
9. (b) Nicolaou, K. C.; Couladouros, E. A.; Nantermet, P. G.; Renaud, J.; Guy, R. K.; Wrasidlo, W. Angew. Chem., Int. Ed. Engl. 1994, 33, 1581.
10. (a) Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395.
11. (b) Kang, S. K.; Jeon, J. H.; Nam, K. S.; Park, C. H.; Lee, H. W. Synth. Commun. 1994, 24, 305.
12. (c) Matsumoto, K.; Fuwa, S.; Kitajima, H. Tetrahedron Lett. 1995, 36, 6499.
13. (d) Shimojo, M.; Matsumoto, K.; Hatanaka, M. Tetrahedron. 2000, 56, 9281.
14. Arakawa, H.; Aresta, M.; Armor, J. N.; Brateau, M. A.; Beckmann, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Dome, K.; DuBois, D. L.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. A.; Goodman, D. W.; Keller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer, L. E.; Marks, T. J.; Morokuma, K.; Nicholas, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Somorjai, G. A.; Stair, P. C.; Stults, B. R.; Tumas, W. Chem. Rev. 2001, 101, 953.
15. Noyori, R. Chem. Commun. 2005, 1807.
16. Lichtenwalter, M.; Cooper, J. F. U.S. Patent 2,773,070, Dec. 4, 1956.
17. (a) Darensbourg, D. J.; Billodeaux, D. R. Inorg. Chem. 2005, 44, 1433.
18. (b) Darensbourg, D. J.; Phelps, A. L. Inorg. Chem. 2005, 44, 4622.
19. (c) Peretti, K. L.; Ajiro, H.; Cohen, C. T.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 11566.
20. (d) Cohen, C. T.; Chu, T.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 10869.
21. (e) Darensbourg, D. J.; Mackiewicz, R. M.; Phelps, A. L.; Billodeaux, D. R. Acc. Chem. Res. 2004, 37, 836.
22. (a) Shen, Y.-M.; Duan, W.-L.; Shi, M. J. Org. Chem. 2003, 68, 1559.
23. (b) Huang, J.-W.; Shi, M. J. Org. Chem. 2003, 68, 1559.
24. (c) Shen, Y.-M.; Duan, W.-L.; Shi, M. Eur. J. Org. Chem. 2004, 69, 3080.
25. (d) Darensbourg, D. J.; Mackiewicz, R. M. J. Am. Chem. Soc. 2005, 27, 14026.
26. Lu, X.-B.; Liang, B.; Zhang, Y.-J.; Tian, Y.-Z.; Wang, Y.-M.; Bai, C.-X.; Wang, H.; Zhang, R. J. Am. Chem. Soc. 2004, 126, 3732.
27. The selectivity factor, s, is determined by using the conversion, C, and ee of the propylene carbonate product in the following equation: s = ln[1 - C(1 + ee)]/ln[1 - C(1 - ee)].
28. For the synthesis and catalytic applications of DIANANE salen complexes see: (a) Berkessel, A.; Schröder, M.; Sklorz, C. A.; Tabanella, S.; Vogl, N.; Lex, J.; Neudörfl, J. M. J. Org. Chem. 2004, 69, 3050.
29. (b) Berkessel, A.; Ertürk, E. Adv. Synth. Catal. 2006, in press.
30. (c) Berkessel, A.; Vogl, N. Eur. J. Org. Chem. 2006, in press.
31. Lu, X.-B.; Shi, L.; Wang Y.-M.; Zhang, R.; Zhang, Y.-J.; Peng, X.-J.; Zhang, Z.-C.; Li, B. J. Am. Chem. Soc. 2006, 128, 1664.
32. Sit, W. N.; Ng, S. M.; Kwong, K. Y.; Lau, C. P. J. Org. Chem. 2005, 70, 8583.
33. PPNF was synthesized from PPNCl by anion exchange (see the Supporting Information).
34. Coates, G. W.; Moore, D. R. Angew. Chem., Int. Ed. 2004, 43, 6618.
35. Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Melchiorre, P.; Sambri, L. Org. Lett. 2005, 7, 1983.
36. Pocker, Y.; Davison, B. L.; Deits, T. L. J. Am. Chem. Soc. 1978, 100, 3564.
37. Verdecchia, M.; Feroci, M.; Palombi, L.; Rossi, L. J. Org. Chem. 2002, 67, 8287.