Enantioselective hydrogenation of α-aryloxy α,β- unsaturated acids. Asymmetric synthesis of α-aryloxycarboxylic acids

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3147-3150

  Maligres, Peter E ^a   Krska, Shane W ^a   Humphrey, Guy R ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKENE; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; ENANTIOSELECTIVITY; HYDROGENATION; SUBSTITUTION REACTION;

EID: 4544296585     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0488035     Document Type: Article

References (56)

1. (a) Secor, J.; Cseke, C.; Owen, W. J. In Biocatalysis in Agricultural Biotechnology; Whitaker, J. R., Sonnet, P. E., Eds.; ACS Symposium Series 389: American Chemical Society: Washington, DC, 1989; pp 265-276.
2. (b) Kikuo, A.; Kiyotaka, Y. Japanese Patent 4202168, 1992.
3. Haskelberg, L. J. Org. Chem. 1947, 12, 423-433.
4. Mathew, N.; Subramanian, S.; Kalyanasundaram, M. Ind. J. Chem. 1996, 55, 40-44.
5. Joshi, K. C.; Bahel, S. C. J. Ind. Chem. Soc. 1960, 37, 365-366.
6. Gualtieri, F.; Bottalico, C.; Calandrella, A.; Dei, S.; Giovannoni, M. P.; Maelli, S.; Romanelli, M. N.; Scapecchi, S.; Teodori, E.; Galeotti, N.; Ghelardini, C.; Giotti, A.; Bartolini, A. J. Med. Chem. 1994, 37, 1712-1719.
7. (a) Amoroso, R.; Bettoni, G.; Tricca, M. L.; Loiodice, F.; Ferorelli, S. Il Farmaco 1998, 53, 73-79.
8. (b) Feller, D. R.; Kamanna, V. S.; Newman H. A. I.; Romstedt, K. J.; Witiak, D. T.; Bettoni, G.; Bryant, S. H.; ConteCamerino, D.; Loiodice, F.: Tortorella, V. J. Med. Chem. 1987, 30, 1265-1270.
9. (a) Bekker, H.; Cassebaum, H.; Leitz, W. Pharmazie 1972, 27, 411-414.
10. (b) Redel, J.; Maillard, J. U.S. Patent 2796432, 1957.
11. (a) Perron, Y. J.; Minor, W. F.; Holdrege, C. T.; Gottstein, W. J.; Godfrey, J. C.; Crast. L. B.; Babel, R. B.; Cheney. L. C. J. Am. Chem. Soc. 1960, 82, 3934-3938.
12. (b) Mejorado, L. H.; Hoarau, C.; Pettus, T. R. R. Org. Lett. 2004, 6, 1535-1538.
13. (a) Kanomata, N.; Nakata, T. J. Chem. Soc. 2000, 122, 4563-4568.
14. (b) Ahmed, F.; Al-Mutairi, E. H.; Avery, K. L.; Cullis, P. M.; Primrose, W. U.; Roberts, G. C. K.; Willis, C. L. J. Chem. Soc., Chem. Commun. 1999, 2046-2050.
15. (c) Macritchie, J. A.; Silcock, A.; Willis, C. L. Tetrahedron: Asymmetry 1997, 8, 3895-3902.
16. (a) Chadha, A.; Manohar, M.; Soundararajan, T.; Lokeswari, T. S. Tetrahedron: Asymmetry 1996, 7, 1571-1572.
17. (b) Dao, D. C.; Okamura, M.; Akasaka, T.; Kawai, Y.; Hida, K.; Ohno, A. Tetrahedron: Asymmetry 1998, 9, 2725-2737.
18. (c) Jian-Xin, G.; Guo-Qiang, L. Tetrahedron 1993, 49, 5805-5816.
19. (a) Devine, P. N.; Dolling, U.-H.; Heid, R. M.; Tschaen, D. M. Tetrahedron Lett. 1996, 37, 2683-2686.
20. (b) Solladie-Cavallo, A.; Benchoqroun, M. Tetrahedron: Asymmetry 1991, 2, 1165-1171.
21. (c) Boireau, G.; Deberly, A. Tetrahedron: Asymmetry 1991, 2, 771-774.
22. (a) Chauvin, R. Tetrahedron: Asymmetry 1990, 1, 737-742.
23. (b) Brown, H. C.; Ramachandran, P. V.; Weissman, S. A.; Swaminathan, S. J. Org. Chem. 1990, 55, 6328-6333.
24. (c) Wang, Z.; La, B.; Fortunak, J. M.; Meng, X.-J.; Kabalka, G. W. Tetrahedron Lett. 1998, 39, 5501-5504.
25. (d) Ramachandran, P. V.; Brown, H. C.; Pitre, S. Org. Lett. 2001, 3, 17-18.
26. (a) Zuo, X.; Liu, H.; Guo, G.: Yang, X. Tetrahedron: Asymmetry 1999, 55, 7787-7804.
27. (b) Wandeler, R.; Kunzle, N.; Schneider, M. S.; Mallat, T.; Baiker, A. J. Chem. Soc., Chem. Commun. 2001, 673-674.
28. (c) Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicolo, F. J. Org. Chem. 2000, 65, 2043-2047.
29. For a recent example employing a Mitsunobu coupling of a phenol with a chiral 2-hydroxyamide see ref 8b.
30. (a) Massolini, G.; Calleri, E.; Lavecchia, A.; Loiodice, F.; Lubda, D.; Temporini, C.; Fracchiolla, G.; Tortorella, P.; Novellino, E.; Caccialanza, G. Anal. Chem. 2003, 75, 535-542.
31. (b) Colton, J. J.; Ahmed, S. N.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 212-217.
32. Kato, D.-I.; Mitsuda, S.; Ohta, H. J. Org. Chem. 2003, 68, 7234-7242.
33. (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synyhesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
34. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
35. (a) Maris, M.; Huck W.-R.; Mallat, T.; Baiker, A. J. Catal. 2003, 52-58.
36. Studer, M.: Wedemeyer-Exl, C.; Spindler, F.; Blaser, H.-U. Monatsh. Chem. 2000, 131, 1335-1343.
37. Kurano, M.; Kondo, Y.; Miura, K.; Usui, T.; Unno. R.; Kakigami, T.; Sawai, K. U.S. Patent 5171865, 1992.
38. α-Acyloxyacrylates, which contain a chelating acyl group, have been enantioselectively hydrogenated using rhodium catalysts, (a) Lotz, M.; Polborn, K.; Knochel, P. Angew. Chem. 2002, 114, 4902-4905. (b) Lotz, M.; Ireland, T.; Perea, J. J. A.; Knochel, P. Tetrahedron: Asymmetry 1999, 10, 1839-1842. (c) Burk. M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345-4353. (d) Schmidt, U.; Langner, J.; Kirschbaum, B.; Braun, C. Synthesis 1994, 1138-1140. The enantioselective hydrogenation of aryl enol ethers is known, (e) Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357-363.
39. α-Acyloxyacrylates, which contain a chelating acyl group, have been enantioselectively hydrogenated using rhodium catalysts, (a) Lotz, M.; Polborn, K.; Knochel, P. Angew. Chem. 2002, 114, 4902-4905. (b) Lotz, M.; Ireland, T.; Perea, J. J. A.; Knochel, P. Tetrahedron: Asymmetry 1999, 10, 1839-1842. (c) Burk. M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345-4353. (d) Schmidt, U.; Langner, J.; Kirschbaum, B.; Braun, C. Synthesis 1994, 1138-1140. The enantioselective hydrogenation of aryl enol ethers is known, (e) Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357-363.
40. α-Acyloxyacrylates, which contain a chelating acyl group, have been enantioselectively hydrogenated using rhodium catalysts, (a) Lotz, M.; Polborn, K.; Knochel, P. Angew. Chem. 2002, 114, 4902-4905. (b) Lotz, M.; Ireland, T.; Perea, J. J. A.; Knochel, P. Tetrahedron: Asymmetry 1999, 10, 1839-1842. (c) Burk. M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345-4353. (d) Schmidt, U.; Langner, J.; Kirschbaum, B.; Braun, C. Synthesis 1994, 1138-1140. The enantioselective hydrogenation of aryl enol ethers is known, (e) Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357-363.
41. α-Acyloxyacrylates, which contain a chelating acyl group, have been enantioselectively hydrogenated using rhodium catalysts, (a) Lotz, M.; Polborn, K.; Knochel, P. Angew. Chem. 2002, 114, 4902-4905. (b) Lotz, M.; Ireland, T.; Perea, J. J. A.; Knochel, P. Tetrahedron: Asymmetry 1999, 10, 1839-1842. (c) Burk. M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345-4353. (d) Schmidt, U.; Langner, J.; Kirschbaum, B.; Braun, C. Synthesis 1994, 1138-1140. The enantioselective hydrogenation of aryl enol ethers is known, (e) Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357-363.
42. α-Acyloxyacrylates, which contain a chelating acyl group, have been enantioselectively hydrogenated using rhodium catalysts, (a) Lotz, M.; Polborn, K.; Knochel, P. Angew. Chem. 2002, 114, 4902-4905. (b) Lotz, M.; Ireland, T.; Perea, J. J. A.; Knochel, P. Tetrahedron: Asymmetry 1999, 10, 1839-1842. (c) Burk. M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345-4353. (d) Schmidt, U.; Langner, J.; Kirschbaum, B.; Braun, C. Synthesis 1994, 1138-1140. The enantioselective hydrogenation of aryl enol ethers is known, (e) Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357-363.
43. (a) Rosnati, V.; Saba, A.; Salimbeni, A. Tetrahedron Lett. 1981, 22, 167-168.
44. (b) Padmanathan, T.; Sultanbawa, M. U. S. J. Chem. Soc. 1963, 4210-4218. X-ray crystallographic data for unsaturated acids 3e and 3f show the stereochemistry of the olefin to be the (Z)-configuration.
45. Prostenik, M.; Salzman, N. P.; Carter, H. E. J. Am. Chem. Soc. 1955, 77, 1856.
46. Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064-3076.
47. (a) Smeets, J. W. H.; Kieboom, A. P. C. Recl. Trac Chim. Pays-Bas 1992, 111, 490-495.
48. (b) Tsuda, Y.; Kawai, K.-I.; Nakajima, S. Chem. Pharm. Bull. 1985, 33, 1955-1960.
49. (c) Piekarski, S. Bull. Soc. Chim. Fr. 1959, 441-445.
50. (d) Matell, M. Ark. Kemi. 1953, 6, 251-255.
51. (a) Stacy, G. W.; Wagner, G. D. J. Am. Chem. Soc. 1952, 74, 909-911.
52. (b) Bachman, G. B. J. Am. Chem. Soc. 1933, 55, 4279-4284.
53. (a) Lloveras, M.; Ramos, I.; Molins, E.; Messeguer, A. Tetrahedron 2000, 56, 3391-3397.
54. (b) Yoshida, M.; Mori, K. Eur. J. Org. Chem. 2000, 1313-1317.
55. (c) Korhonen, I. O. O.; Pitkanen, M.; Korvola, J. N. J. Tetrahedron 1982, 38, 2837-2841.
56. 2.