Synthesis of both enantiomers of hemiesters by enantioselective methanolysis of meso cyclic anhydrides catalyzed by α-amino acid-derived chiral thioureas

Journal of Organic Chemistry

Volumn 75, Issue 15, 2010, Pages 5417-5420

  Manzano, Rubén ^a   Andrés, José M ^a   Muruzábal, María Dolores ^a   Pedrosa, Rafael ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLYSIS; BIFUNCTIONAL; CATALYST LOADINGS; D-VALINE; DESYM-METRIZATION; ENANTIOMERIC RATIO; ENANTIOSELECTIVE; METHANOLYSIS; ORGANOCATALYSTS; QUANTITATIVE YIELDS;

AMINO ACIDS; CATALYSTS; CHIRALITY; ORGANIC ACIDS; THIOUREAS; UREA;

ENANTIOMERS;

ALPHA AMINO ACID; ESTER DERIVATIVE; THIOUREA DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; ENANTIOMER; METHANOLYSIS; SYNTHESIS;

AMINO ACIDS; ANHYDRIDES; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METHANE; STEREOISOMERISM; THIOUREA;

EID: 77955137826     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100792r     Document Type: Article

References (51)

1. Bernardi, A.; Arosio, D.; Dellavecchia, D.; Micheli, F. Tetrahedron: Asymmetry 1999, 10, 3403
2. Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793
3. Choi, C.; Tian, S.-K.; Deng, L. Synthesis 2001, 1737
4. Hameršak, Z.; Stipetić, I.; Avdagić, A. Tetrahedron: Asymmetry 2007, 18, 1481
5. Röme, D.; Johansson, M.; Sterner, O. Tetrahedron Lett. 2007, 48, 635
6. Huang, J.; Xiong, F.; Chen, F.-E. Tetrahedron: Asymmetry 2008, 19, 1436
7. For reviews on that topic see: Spivey, A. C.; Andrews, B. I. Angew. Chem., Int. Ed. 2001, 40, 3131
8. Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965
9. Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621
10. Atodiresei, I.; Schiffers, I.; Bolm, C. Chem. Rev. 2007, 107, 5683
11. Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1993, 58, 142
12. Kraft, P.; Cadalbert, R. Synthesis 1998, 1662
13. Gourdel-Martin, M.-E.; Comoy, C.; Huet, F. Tetrahedron: Asymmetry 1999, 10, 403
14. Dai, W. M.; Yeung, K. K. Y.; Chow, C. W.; Williams, I. D. Tetrahedron: Asymmetry 2001, 12, 1603
15. Hiratake, J.; Yamamoto, Y.; Oda, J. J. Chem. Soc., Chem. Commun. 1985, 1717
16. Hiratake, J.; Inagaki, M.; Yamamoto, Y.; Oda, J. J. Chem. Soc., Perkin Trans. I 1987, 1053
17. Aitken, R. A.; Gopal, J.; Hirst, J. A. J. Chem. Soc., Chem. Commun. 1988, 632
18. Aitken, R. A.; Gopal, J. Tetrahedron: Asymmetry 1990, 1, 517
19. Bolm, C.; Schiffers, I.; Dinter, C. L.; Gerlach, A. J. Org. Chem. 2000, 65, 6984
20. Tanyeli, C.; Özubuku, S. Tetrahedron: Asymmetry 2003, 14, 1167
21. Bolm, C.; Schiffers, I.; Atodiresei, I.; Hackenberger, C. P. R. Tetrahedron: Asymmetry 2003, 14, 3455.
22. Bolm, C.; Atodiresei, I.; Schiffers, I. Org. Synth. 2005, 82, 120.
23. Ishii, Y.; Fujimoto, R.; Mikami, M.; Murakami, S.; Miki, Y.; Furukawa, Y. Org. Process Res. Dev. 2007, 11, 609
24. Ivšić, T.; Hameršak, Z. Tetrahedron: Asymmetry 2009, 20, 1095
25. Chen, Y.; Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2000, 122, 9542
26. Bigi, F.; Carloni, S.; Maggi, R.; Mazzacani, A.; Sartori, G.; Tanzi, G. J. Mol. Catal. A: Chem. 2002, 182-183, 533
27. Song, Y.-M.; Choi, J. S.; Yang, J. W.; Han, H. Tetrahedron Lett. 2004, 45, 3301
28. Kim, H. S.; Song, Y.-M.; Choi, J. S.; Yang, J. W.; Han, H. Tetrahedron 2004, 60, 12051
29. Uozumi, Y.; Yasoshima, K.; Miyachi, T.; Nagai, S.-I. Tetrahedron Lett. 2001, 42, 411
30. Okamatsu, T.; Irie, R.; Katsuki, T. Synlett 2007, 1569
31. Yamamoto, K.; Nishioka, T.; Oda, J. Tetrahedron Lett. 1988, 29, 1717
32. Ozegowski, R.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1993, 4, 695
33. Fryszkowska, A.; Frelek, J.; Ostaszewski, R. Tetrahedron 2005, 61, 6064
34. Fryszkowska, A.; Komar, M.; Koszelewski, D.; Ostaszewski, R. Tetrahedron: Asymmetry 2005, 16, 2475
35. Fryszkowska, A.; Komar, M.; Koszelewski, D.; Ostaszewski, R. Tetrahedron: Asymmetry 2006, 17, 961
36. Oh, S. H.; Rho, H. S.; Lee, J. W.; Lee, J. E.; Youk, S. H.; Chin, J.; Song, C. E. Angew. Chem., Int. Ed. 2008, 47, 7872
37. Youk, S. H.; Oh, S. H.; Rho, H. S.; Lee, J. E.; Lee, J. W.; Song, C. E. Chem. Commun. 2009, 2220
38. Honjo, T.; Sano, S.; Shiro, M.; Nagao, Y. Angew. Chem., Int. Ed. 2005, 44, 5838
39. For recent reviews on this topic see: Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289
40. Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299
41. Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999
42. Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520
43. Connon, S. J. Chem.- Eur. J. 2006, 12, 5418
44. Takemoto, Y.; Miyabe, H. Chimia 2007, 61, 269
45. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
46. Sohtome, Y.; Nagasawa, K. Synlett 2010, 1
47. Peschiulli, A.; Quigley, C.; Tallon, S.; Gunko, Y. K.; Connon, S. J. J. Org. Chem. 2008, 73, 6409
48. Wang, S.-X.; Chen, F.-E. Adv. Synth. Catal. 2009, 351, 547
49. Peschiulli, A.; Gunko, Y.; Connon, S. J. J. Org. Chem. 2008, 73, 2454
50. Andrés, J. M.; Manzano, R.; Pedrosa, R. Chem.- Eur. J. 2008, 14, 5116
51. Rho, H. S.; Oh, S. H.; Lee, J. W.; Lee, J. Y.; Chin, J.; Song, C. E. Chem. Commun. 2008, 1208