Highly efficient and practical selective monohydrolysis of symmetric diesters: Recent progress and scope

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 66, Issue 10, 2008, Pages 983-994

  Niwayama, Satomi ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

Carboxylic acid; Desymmetrizatoin; Ester; Green reaction; Half ester; Monohydrolysis; Selectivity; Symmetric diester; Water mediated reaction

Indexed keywords

CARBOXYLIC ACIDS; CATALYST SELECTIVITY; MIXTURES;

DESYMMETRIZATOIN; DIESTERS; GREEN REACTION; MEDIATED REACTIONS; MONOHYDROLYSIS;

ESTERS;

EID: 58249106365     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.66.983     Document Type: Review

References (58)

1. This work is the subject of U.S. and international patent applications. See S. Niwayama, U.S. Serial No. 12/156, 448 and PCT/US 08/06907
2. For example, (a) E. J. Corey, J. Am. Chem. Soc., 74, 5897 (1952);
3. (b) A. Vecchi, G. Melone, J. Org. Chem., 24, 109 (1959);
4. (c) R. E. Strube, Org. Synth., Col. Vol. IV, 417 (1963);
5. (d) A. Robertson, W. F. Sandrock, J. Chem. Soc., 1933, 1617;
6. (e) V. Grakauskas, A. M. Guest, J. Org. Chem., 43, 3485 (1978);
7. (f) C. R. Hutchinson, M. Nakane, H. Gollman, P. L. Knutson, Org. Synth., Collect. Vol. 7, 323, Wiley, New York, NY, (1990);
8. (g) J. Westermann, M. Schneider, J. Platzek, O. Petrov, Organic Process Research & Development, 11, 200 (2007);
9. (h) A. de Meijere, K. Ernst, B. Zuck, M. Brandi, S. I. Kozhushkow, M. Tamm, D. S. Yufit, J. A. K. Howard, T. Labahn, Eur. J. Org. Chem., 11, 3105 (1999);
10. (i) N. De Kimpe, M. Boeykens, K. A. Tehrani, ibid., 59, 8215 (1994);
11. (j) P. E. Eaton, N. Nordari, J. Tsanaktsidis, S. P. Upadhyaya, Synthesis, 1995, 501
12. For example, (a) J. Hiratake, Y. Yamamoto, J. Oda, J. Chem. Soc., Chem. Commun., 1985, 1717;
13. (b) P. D. Theisen, C. H. Heathcock, J. Org. Chem., 58, 142 (1993);
14. (c) T. Albers, S. C. G. Biagini, D. E. Hibbs, M. B. Hursthouse, K. M. A. Malik, M. North, E. Uriarte, G. Zagotto, Synthesis, 1996, 393;
15. (d) C. Bolm, A. Gerlach, C. L. Dinter, Synlett, 1999, 195;
16. (e) G. Sabitha, R. Srividya, J. S. Yadav, Tetrahedron, 55, 4015 (1999);
17. (f) C. Bolm, C. L. Dinter, A. Seger, H. Höcker, J. Brozio, J. Org. Chem., 64, 5730 (1999)
18. (a) S. Niwayama, J. Org. Chem., 65, 5834 (2000);
19. (b) Chemical and Engineering News, January 22, 90 (2001)
20. (a) S. Niwayama, Tetrahedron Lett., 41, 10163 (2000);
21. (b) S. Niwayama, H. Cho, unpublished results 6) This "conformational lock" due to electrostatic interaction between carboalkoxy groups and other functional groups to explain diastereoselectivity has been reported. For example, (a) Y. Yamamoto, H. Nemoto, R. Kikuchi, H. Komatsu, I. Suzuki, J. Am. Chem. Soc., 112, 8598 (1990);
22. (b) Y. Yamamoto, K. Taniguchi, K. Maruyama, J. Chem. Soc., Chem. Commun., 1985, 1429;
23. (c) Y. Yamamoto, Y. Chounan, S. Nishi, T. Ibuka, H. Kitabara, J. Am. Chem. Soc., 114, 7652 (1992)
24. H. Cho, S. Niwayama, 63 rd Southwest Regional Meeting of the American Chemical Society, #31 (2007)
25. S. Niwayama, Y. Inouye, M. Eastman, Tetrahedron Lett., 40, 5961 (1999)
26. S. Niwayama, H. Wang, Y. Hiraga, J. C. Clayton, Tetrahedron Lett., 48, 8508 (2007)
27. THF-water mixtures are known to form hydrates at a low temperature. For example, (a) T. Iida, H. Mori, T. Mochizuki, Y. H. Mori, Chemical Engineering Science 56, 4747 (2001);
28. (b) T. Makino, T. Sugahara, K. Ohgaki, J. Chem. Eng. Data, 50, 2058 (2005)
29. For example, (a) P. Haberfield, J. Friedman, M. F. Pinkston, J. Am. Chem. Soc., 94, 71 (1999);
30. (b) D. D. Roberts, J. Org. Chem., 31, 4037 (1966)
31. Other examples of water-mediated desymmetrization can be found in the following references: (a) J. M. Chong, M. A. Heuft, P. Rabbat, J. Org. Chem., 65, 5837 (2000);
32. (b) I. Rubinstein, K. Kjaer, I. Weissbuch, M. Lahav, Chem. Commun., 2005, 5432;
33. (c) Z.-B. Luo, X.-L. Hou, L.-X. Dai, Tetrahedron: Asymmetry, 18, 443 (2007);
34. (d) C. Ogawa, N. Wang, M. Boudou, S. Azoulay, K. Manabe, S. Kobayashi, Heterocycles, 72, 589 (2007)
35. S. Niwayama, A. Rimkus, Bull. Chem. Soc. Jpn., 78, 498 (2005)
36. Y. Hiraga, S. Niwayama, unpublished results
37. For example, (a) A. Bulychev, J. R. Bellettini, M. O'Brien, P. J. Crocker, J.-P. Samama, M. J. Miller, S. Mobashery, Tetrahedron, 56, 5719 (2000);
38. (b) R. Bihovsky, I. Pendrak, Bioorg. Med. Chem. Lett., 6, 1541 (1996);
39. (c) M. Horikawa, H. Shirahama, Synlett, 1, 95 (1996);
40. (d) G. Keum, C. H. Hwang, S. B. Kang, Y. Kim, E. Lee, J. Am. Chem. Soc., 127, 10396 (2005);
41. (e) H.-J. Kim, J. Lindsey, J. Org. Chem., 70, 5475 (2005);
42. (f) H.-J. Knoelker, M. Wolpert, Tetrahedron Lett., 38, 533 (1997);
43. (g) S. Marcaccini, R. Pepino, M. C. Pozo, S. Basurto, M. Garcia-Valverde, T. Torroba, ibid., 45, 3999 (2004);
44. (h) B. List, A. Doehring, M. T. Hechavarria Fonseca, A. Job, R. Rios Torres, Tetrahedron, 62, 476 (2006);
45. (i) D. R. Williams, D. C. Kammler, R. F. Goundry, Heterocycles, 67, 555 (2006)
46. (a) B. Rigo, D. Fasseur, P. Cauliez, D. Couturier, Tetrahedron Lett., 30, 3073 (1989);
47. (b) H. Junek, E. Ziegler, U. Herzog, H. Kroboth, Synthesis, 1976, 332
48. S. Niwayama, H. Cho, C. Lin, Tetrahedron Lett., 49, 4434 (2008)
49. S. Niwayama, H. Cho, Manuscript submitted for publication
50. S. Niwayama, H. Cho, Unpublished results
51. For example, (a) S. Inagaki, H. Fujimoto, K. Fukui, J. Am. Chem. Soc., 98, 4054 (1976);
52. (b) P. v. R. Schleyer, ibid., 89, 701 (1967);
53. (c) N. G. Rondan, M. N. Paddon-Row, P. Caramella, K. N. Houk, ibid., 103, 2436 (1981);
54. (d) T. Ohwada, Tetrahedron, 49, 7649 (1993);
55. (e) F. Freeman, Chem. Rev., 75, 439 (1975);
56. (f) H. C. Brown, S. Krishnamurthy, J. Am. Chem. Soc., 94, 7159 (1972)
57. (a) S. Niwayama, H. Cho, manuscript in preparation.
58. (b) S. Niwayama, Y. Hiraga, Tetrahedron Lett., 44, 8567 (2003)