Enantioselective synthetic method for α-alkylserine via phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4- carbonylcamphorsultam

Journal of Organic Chemistry

Volumn 70, Issue 10, 2005, Pages 4158-4161

  Lee, Jihye ^a   Lee, Yeon Im ^a   Kang, Myoung Joo ^a   Lee, Yeon Ju ^a   Jeong, Byeong Seon ^a   Lee, Jeong Hee ^a   Kim, Mi Jeong ^a   Choi, Ji Yeon ^a   Ku, Jin Mo ^a   Park, Hyeung Geun ^a   Jew, Sang Sup ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; HYDROLYSIS; PHASE TRANSITIONS;

CATALYTIC ALKYLATION; PHASE-TRANSFER CATALYTIC ALKYLATION; SYNTHETIC METHOD;

SYNTHESIS (CHEMICAL);

2 PHENYL 2 OXAZOLINE 4 CARBONYLCAMPHORSULTAM; CAMPHOR DERIVATIVE; CARBONYL DERIVATIVE; OXAZOLINE DERIVATIVE; SERINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROLYSIS; SYNTHESIS;

ALKYLATION; CARBOXYLIC ACIDS; ESTERS; EUGENOL; MODELS, CHEMICAL; OXAZOLES; SERINE; STEREOISOMERISM;

EID: 21044455589     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050197j     Document Type: Article

References (43)

1. (a) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
2. (b) Cativiela, C.; Diaz-de-Villegas, M. D. T. Tetrahedron: Asymmetry 1998, 9, 3517.
3. (c) Cativiela, C.; Diaz-de-Villegas, M. D. T. Tetrahedron: Asymmetry 2000, 11, 645.
4. (a) Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Précigoux, G.; Aubry, A.; Kamphius, J. Biopolymers 1993, 33, 1061.
5. (b) Karle, I. L.; Rao, R. B.; Prasad, S.; Kaul, R.; Balaram, P. J. Am. Chem. Soc. 1994, 116, 10355.
6. (c) Formaggio, F.; Pantano, M.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Kamphius, J. J. Chem. Soc., Perkin Trans. 2 1995, 1097.
7. (d) Benedetti, E. Biopolymers 1996, 40, 3.
8. (e) Karle, I. L.; Kaul, R.; Rao, R. B.; Raghothama, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 12048.
9. (a) Barrett, G. C. Amino Acids, Peptides and Proteins; The Chemical Society: London, 1980; Vol. 13, p 1.
10. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: London, 1985; p 55.
11. (c) Richardson, J. S. Biophysik. J. 1992, 63, 1186.
12. (d) Mickos, H.; Sundberg, K.; Luning, B. Acta Chem. Scand. 1992, 46, 989.
13. (e) Gante, J. Angew. Chem., Int. Ed. 1994, 33, 1699.
14. (a) Fujita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sasaki, S.; Toyama, R.; Yoneta, M.; Chiba, K.; Hosino, Y.; Okumoto, T. J. Antibiot. 1994, 47, 216.
15. (b) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113.
16. (c) Omura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge, K; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117.
17. (d) Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 557.
18. (e) Kawatsu, M.; Yamashita, T.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1995, 48, 222.
19. Previous synthetic methods of chiral α-alkylserines are cited in ref 7.
20. Park, H.-g.; Lee, J.; Kang, M. J.; Lee, Y.-J.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Kim, M.-J.; Choi, S.-h.; Jew, S.-s. Tetrahedron 2004, 60, 4243.
21. Jew, S.-s.; Lee, Y.-J.; Lee, J.; Kang, M. J.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Kim, M.-J.; Choi, S.-h.; Ku, J.-M.; Park, H.-g. Angew. Chem., Int. Ed. 2004, 43, 2382.
22. For our recent reports on the enantioselective phase-transfer catalytic alkylation, see: (a) Jew, S.-s.; Jeong, B.-S.; Yoo, M.-S.; Huh, H.; Park, H.-g. Chem. Commun. 2001, 1244.
23. (b) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Park, M.-K; Huh, H.; Jew, S.-s. Tetrahedron Lett. 2001, 42, 4645.
24. (c) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, M.-K.; Lee, Y.-J.; Kim, M.-J.; Jew, S.-s. Angew. Chem., Int. Ed. 2002, 41, 3036.
25. (d) Jew, S.-s.; Yoo, M.-S.; Jeong, B.-S.; Park, I. Y.; Park, H.-g. Org. Lett. 2002, 4, 4245.
26. (e) Park, H.-g.; Jeong, B.-S.; Yoo, M.-S.; Lee, J.-H.; Park, B.-s.; Kim, M. G.; Jew, S.-s. Tetrahedron Lett. 2003, 44, 3497.
27. (f) Lee, Y.-J.; Lee, J.; Kim, M.-J.; Kim, T.-S.; Park, H.-g.; Jew, S.-s. Org. Lett. 2005, 7, 1557.
28. (a) Josien, H.; Martin, A.; Chassaing, G. Tetrahedron Lett. 1991, 32, 6547.
29. (b) Josien, H.; Chassaing, G. Tetrahedron: Asymmetry 1992, 3, 1351.
30. (c) Josien, H.; Lavielle, S.; Brunissen, A.; Saffroy, M.; Torrens, Y.; Beaujouan, J.-C.; Glowinski, J.; Chassaing, G. J. Med. Chem. 1994, 37, 1586.
31. (d) Guillena, G.; Najera, C. Tetrahedron: Asymmetry 1998, 9, 3935.
32. Compound 5 was prepared from ethyl benzimidate and serine methyl ester on the basis of previous methods (95%).
33. (a) Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 18, 4171.
34. (b) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 6009.
35. Singh, S.; Rao, S. J.; Pennington, M. W. J. Org. Chem. 2004, 69, 4555.
36. Blarer, S. J. Tetrahedron Lett. 1985, 26, 4055.
37. Diastereomeric excess (de) of the alkylation products was determined by the chiral HPLC analysis of the corresponding methyl 2-phenyl-2-oxazoline-4- alkyl-carboxylates. Representative procedure for transformation to the methyl ester is explained in Supporting Information.
38. (a) Schwesinger, R. Chimia 1985, 39, 269.
39. (b) Schwesinger, R.; Schlemper, H. Angew. Chem., Int. Ed. 1987, 26, 1167.
40. (a) Zhang, J.; Flippen-Anderson, J. L.; Kozikowski, A. P. J. Org. Chem. 2001, 66, 7555.
41. (b) Choudhury, P. K.; Le Nguyen, B. K.; Laglois, N. Tetrahedron Lett. 2002, 43, 463.
42. (c) Kawasaki, M.; Namba, K.; Tsujishima, H.; Sinada, T.; Ohfune, Y. Tetrahedron Lett. 2003, 44, 1235.
43. Calculations were done using the program SYBYL 6.5 from Tripos Software, Inc., St. Louis, MO. The four-enolate conformers were minimized using Tripos force field parameters and the conjugate gradient algorithm with a gradient convergence value of 0.005 kcal/mol Å. Partial atomic charges were calculated using the Gasteiger-Huckel method. The low-energy conformation was searched by the grid search method.