Highly enantioselective decarboxylative protonation of α- aminomalonates mediated by thiourea Cinchona alkaloid derivatives: Access to both enantiomers of cyclic and acyclic α-aminoacids

Organic Letters

Volumn 9, Issue 14, 2007, Pages 2621-2624

  Amere, Mukkanti ^a   Lasne, Marie Claire ^a   Rouden, Jacques ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINO ACID; CARBOXYLIC ACID; MALONIC ACID DERIVATIVE; PROTON; QUININE; SOLVENT; THIOUREA;

ARTICLE; CHEMISTRY; CINCHONA; DECARBOXYLATION; STEREOISOMERISM;

ACIDS, ACYCLIC; ALKALOIDS; AMINO ACIDS; AMINO ACIDS, CYCLIC; CINCHONA; DECARBOXYLATION; MALONATES; PROTONS; QUININE; SOLVENTS; STEREOISOMERISM; THIOUREA;

EID: 34547408925     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070712v     Document Type: Article

References (43)

1. (a) Marckwald, W. Ber. Dtsch. Chem. Ges. 1904, 37, 349.
2. (b) Marckwald, W. Ber. Dtsch. Chem. Ges. 1904, 37, 1368.
3. (a) Verbit, L.; Halbert, T. R.; Patterson, R. B. J. Org. Chem. 1975, 40, 1649-1650.
4. (b) Glusker, J. P.; Carrell, H. L.; Job, R.; Bruice, T. C. J. Am. Chem. Soc. 1974, 96, 5741-5751.
5. (c) Yashiro, M.; Ajioka, M.; Yano, S.; Toriumi, K.; Ito, T.; Yoshikawa, S. Inorg. Chem. 1986, 25, 1709-1715.
6. (d) Toussaint, O.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1987, 28, 539-542.
7. (e) Roy, O.; Dieckmann, M.; Riahi, A.; Hénin, F.; Muzart, J. Chem. Commun. 2001, 533-534.
8. (f) Baur, M. A.; Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron: Asymmetry 2003, 14, 2755-2761.
9. (g) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986-3994.
10. (a) Miyamoto, K.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 4077-4078.
11. (b) Sugai, T.; Ohta, H. Chem. Commun. 2000, 1519-1520.
12. (c) Matoishi, K.; Ueda, M.; Miyamoto, K.; Ohta, H. J. Mol. Catal. B: Enzym. 2004, 27, 161-168.
13. (d) Ijima, Y.; Matoishi, K.; Terao, Y.; Doi, N.; Yanagawa, H.; Ohta, H. Chem. Commun. 2005, 877-879.
14. (e) Terao, Y.; Ijima, Y.; Miyamoto, K.; Ohta, H. J. Mol. Catal. B: Enzym. 2007, 45, 15-20.
15. Mohr, J. T.; Nishimata, T.; Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 11348-11349.
16. (a) Brunner, H.; Schmidt, P. Eur. J. Org. Chem. 2000, 2119-2133.
17. (b) Brunner, H.; Baur, M. A. Eur. J. Org. Chem. 2003, 2854-2862.
18. (c) Seitz, T.; Baudoux, J.; Bekolo, H.; Cahard, D.; Plaquevent, J.-C.; Lasne, M.-C.; Rouden, J. Tetrahedron 2006, 62, 6155-6165.
19. (a) Martin, J.; Deagostino, A.-M.; Perrio, C.; Dauphin, F.; Ducandas, C.; Morin, C.; Desbène, P.-L.; Lasne, M.-C. Bioorg. Med. Chem. 2000, 8, 591-601.
20. (b) Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181-7182.
21. Rogers, L. M.-A.; Rouden, J.; Lecomte, L.; Lasne, M.-C. Tetrahedron Lett. 2003, 44, 3047-3050.
22. Selected bifunctional organocatalysis: (a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672-12673.
23. (b) Okino, T.; Nakamura, Y.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625-627.
24. (c) Hoashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem., Int. Ed. 2005, 44, 4032-4035.
25. (d) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X. N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119-125.
26. (e) Li, H. M.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906-9907.
27. (f) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105-108.
28. (g) Li, H.; Song, J.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2005, 127, 8948-8849.
29. (h) Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680-3681.
30. (i) Shi, M.; Chen, L. H.; Li, C. Q. J. Am. Chem. Soc. 2005, 127, 3790-3800.
31. (j) Berkessel, A.; Cleemann, F.; Mukherjee, S.; Muller, T. N.; Lex, J. Angew. Chem., Int. Ed. 2005, 44, 807-811.
32. (k) Berkessel, A.; Mukherjee, S.; Cleemann, F.; Muller, T. N.; Lex, L Chem. Commun. 2005, 1898-1900.
33. (l) Lattanzi, A. Org. Lett. 2005, 7, 2579-2582.
34. Thiourea catalysts of cinchona alkaloids: (a) Tillman, A. L.; Ye, J.; Dixon, D. J. Chem. Commun. 2006, 1191-1193.
35. (b) Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481-4483.
36. (c) McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367-6370.
37. (d) Vakulya, B.; Varga, S.; Csampai, A.; Soós, T. Org. Lett. 2005, 7, 1967-1969.
38. (e) Marcelli, T.; van der Haas, R. N. S.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 929-931.
39. Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048-6049.
40. Connon, S. J. Chem. Eur. J. 2006, 12, 5418-5427.
41. Absolute stereochemistry was determined by comparison with known data (ref 5). New compounds were independently synthesized from the corresponding optically pure aminoacids.
42. 3 sample kept at rt for 7 days, whereas no decarboxylation was observed with 7a, 11a, or 15a under the same conditions. This suggests that the sulfur atom of the thiophene ring is basic enough to promote self-decarboxylation.
43. This result is similar to our previous attempt of a catalytic reaction with substrate 7a. 7b was obtained with 72% ee with use of 10% of epicinchonine at room temperature, see ref 5c.