Copper catalyzed asymmetric synthesis of chiral allylic esters

Journal of the American Chemical Society

Volumn 128, Issue 49, 2006, Pages 15572-15573

  Geurts, Koen ^a   Fletcher, Stephen P ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; COPPER; ESTER DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 33845443952     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065780b     Document Type: Article

References (41)

1. Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761-1795.
2. For example, see: (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2226-2254.
3. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Wiley-VHC: New York, 2000: Chapter 6.
4. (c) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628-1629.
5. (a) Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta. 1992, 75, 170-173.
6. (b) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 8355-8361.
7. (c) For a general review, see Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824.
8. Tomita, D.; Kanai, M.; Shibasaki, M. Chem. Asian J. 2006, 1-2, 161-166.
9. (a) Trost, B. M.; Aponick, A. J. Am. Chem. Soc. 2006, 128, 3931-3933.
10. (b) Trost, B. M.; Machacek, M. R.; Faulk, B. D. J. Am. Chem. Soc. 2006, 128, 6745-6754.
11. (c) Trost, B. M.; Tsui, H.-C.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 3534-3535.
12. (d) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545-4554.
13. (e) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702-12703.
14. (a) Shu, C.; Hartwig, J. F. Angew. Chem. Int. Ed. 2004, 43, 4794-4797.
15. (b) López, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426-3427.
16. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414.
17. Kirsch, S. F.; Overman, L. E. J. Am. Chem. Soc. 2005, 127, 2866-2867.
18. For chiral allylic amines see: Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413.
19. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 2001, 123, 3671-3686.;
20. J. Am. Chem. Soc. 2001, 123, 3687-3696.;
21. J. Am. Chem. Soc. 2001, 123, 12191-12201.
22. For leading references on AAA: Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
23. López, F.; van Zijl, A. W.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2006, 409-411.
24. For recent reviews on Cu-catalyzed AAA, see: (a) Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 4435-4439.
25. (b) Alexakis, A.; Malan, C.; Lea, L.; Tissot-Croset, K.; Polet, D.; Falciola, C. Chimia 2006, 60, 124-130.
26. See supporting information.
27. (a) Des Mazery, R.; Pullez, M.; López, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 9966-9967.
28. (b) López, F.; Harutyunyan, S. R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2005, 44, 2752-2756.
29. (c) Lopez, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2004, 126, 12784-12785.
30. (d) Feringa, B. L.; Badorrey, R.; Pena, D.; Harutyunyan, S. R.; Minnaard, A. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5834-5838.
31. The formation of 2 and 3 are both copper-catalyzed as a control experiment (Table 1, entry 11) in the absence of copper salt, provided no detectable amount of 2 or 3.
32. (a) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
33. (b) van Zijl, A. W.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Adv. Synth. Catal. 2004, 346, 413-420.
34. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353
35. Multistep routes to optically pure 1-buten-3-ol: (a) Balmer, E.; Germain, A.; Jackson, W. P.; Lygo, B. J. Chem. Soc., Perkin Trans. 1 1993, 399-400.
36. (b) Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J.; Pflum, D. A.; Petsch, D. T. J. Am. Chem. Soc. 1997, 119, 9641-9651;
37. Klinger, F. D.; Psiorz, M. German patent DE-4219510-C1, 1993. It has been noted that successful kinetic resolutions of low molecular weight allylic alcohols are conspicuously absent in reviews of the Sharpless epoxidation;
38. Faller, J. W.; Wilt, J. C.; Parr, J. Org. Lett. 2004, 6, 1301-1304.
39. A practical route to optically pure 6 for use as a starting material in natura product synthesis was developed (7 steps): Takayama, H.; Fujiwara, R.; Kasai, Y.; Kitajima, M.; Aimi, N. Org. Lett. 2003, 5, 2967-2970.
40. Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
41. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.