Asymmetric synthesis of anti -β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters

Organic Letters

Volumn 15, Issue 10, 2013, Pages 2446-2449

  Goodman, C Guy ^a   Do, Dung T ^a   Johnson, Jeffrey S ^a  

^a The University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ESTER; OXOACID; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CATALYSIS; ESTERS; KETO ACIDS; KINETICS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RUTHENIUM; STEREOISOMERISM;

EID: 84877892720     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4009206     Document Type: Article

References (46)

1. Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44
2. Etoh, Y.; Miyazaki, M.; Saitoh, H.; Toda, N. Jpn. J. Pharmacol. 1993, 63, 109-119
3. Suda, H.; Takita, T.; Aoyagi, T.; Umezawa, H. J. Antibiot. 1976, 29, 100-101
4. Saiki, I.; Murata, J.; Watanabe, K.; Fujii, H.; Abe, F.; Azuma, I. Jpn. J. Cancer Res. 1989, 80, 873-878
5. Ojima, I.; Das, M. J. Nat. Prod. 2009, 72, 554-565
6. Deng, L.; Jacobsen, E. N. J. Org. Chem. 1992, 57, 4320-4323
7. Righi, G.; Rumboldt, G. J. Org. Chem. 1996, 61, 3557-3560
8. Jang, S. H.; Kim, J. Y.; Kim, M. K.; Han, J. W.; Park, K. H.; Yoon, Y. J; Lee, S.-G. Bull. Korean Chem. Soc. 2009, 30, 163-171
9. Sharpless, K. B.; Chong, A. O.; Oshima, K. J. Org. Chem. 1976, 41, 177-179
10. Herranz, E.; Sharpless, K. B. J. Org. Chem. 1978, 43, 2544-2548
11. Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454
12. O'Brien, P. Angew. Chem., Int. Ed. 1999, 111, 326-329
13. Harris, L.; Mee, S. P. H.; Furneaux, R. H.; Gainsford, G. J.; Luxenburger, A. J. Org. Chem. 2011, 76, 358-372
14. Jiang, Y.; Chen, X.; Zheng, Y.; Xue, Z.; Shu, C.; Yuan, W.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 7304-7307
15. Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2005, 127, 9360-9361
16. Borah, J. C; Gogoi, S.; Boruwa, J.; Kalita, B.; Barua, N. C. Tetrahedron Lett. 2004, 45, 3689-3691
17. Dziedzic, P.; Vesely, J.; Córdova, A. Tetrahedron Lett. 2008, 49, 6631-6634
18. Dziedzic, P.; Schyman, P.; Kullberg, M.; Córdova, A. Chem.-Eur. J. 2009, 15, 4044-4048
19. Juhl, K.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420-2421
20. For a specific example, see: Torssell, S.; Kienle, M.; Somfai, P. Angew. Chem., Int. Ed. 2005, 44, 3096-3099
21. Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117-128
22. Enantioselective Synthesis of β-Amino Acids, 2 nd ed.; Juaristi, E.; Soloshonok, V., Eds.; Wiley: Hoboken, NJ, 2005.
23. Sleebs, B. E.; Nguyen, T. V.; Hughes, A. B. Org. Prep. Proced. Int. 2009, 41, 429-478
24. Steward, K. M.; Gentry, E. C.; Johnson, J. S. J. Am. Chem. Soc. 2012, 134, 7329-7332
25. Steward, K. M.; Corbett, M. T.; Goodman, C. G.; Johnson, J. S. J. Am. Chem. Soc. 2012, 134, 20197-20206
26. Corbett, M. T.; Johnson, J. S. J. Am. Chem. Soc. 2013, 135, 594-597
27. Hamada, Y. Chem. Pharm. Bull. 2012, 60, 1-20
28. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, A. N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134-9135
29. Mordant, C.; Dünkelmann, P.; Ratovelomanana-Vidal, V.; Genet, J.-P. Eur. J. Org. Chem. 2004, 3017-3026
30. Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Angew. Chem., Int. Ed. 2004, 43, 882-884
31. Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Tetrahedron: Asymmetry 2008, 19, 2816-2828
32. Liu, Z.; Schults, C. S.; Sherwood, C. A.; Krska, S.; Dormer, P. G.; Desmond, R.; Lee, C.; Sherer, E. C.; Shpungin, J.; Cuff, J.; Xu, F. Tetrahedron Lett. 2011, 52, 1685-1688
33. Seashore-Ludlow, B.; Villo, P.; Häcker, C.; Somfai, P. Org. Lett. 2010, 12, 5274-5277
34. Patel, R. N.; Banerjee, A.; Howell, J. M.; McNamee, C. G.; Brozozowski, D.; Mirfakhrae, D.; Nanduri, V.; Thottathil, J. K.; Szarka, L. J. Tetrahedron: Asymmetry 1993, 4, 2069-2084
35. Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696-9697
36. DiRocco, D. A; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 5904-5906
37. Vora, H. U.; Lathrop, S. P.; Reynolds, N. T.; Kerr, M. S.; Read de Alaniz, J.; Rovis, T. Org. Synth. 2010, 87, 350-361
38. Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562-7563
39. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522
40. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102
41. Fringuelli, F.; Pizzo, F.; Rucci, M.; Vaccaro, L. J. Org. Chem. 2003, 68, 7041-7045
42. Trost, B. M.; Malhotra, S.; Ellerbrock, P. Org. Lett. 2013, 15, 440-443
43. Prévost, S.; Gauthier, S.; Caño de Andrade, M. C.; Mordant, C.; Touati, A. R.; Lesot, P.; Savignac, P.; Ayad, T.; Phansavath, P.; Ratovelomanana-Vidal, V.; Geneît, J.-P. Tetrahedron: Asymmetry 2010, 21, 1436-1446
44. Sepe, V.; D'Auria, M. V.; Bifulco, G.; Ummarino, R.; Zampella, A. Tetrahedron 2010, 66, 7520-7526
45. Zhao, Y.; Jiang, N.; Chen, S.; Peng, C.; Zhang, X.; Zou, Y.; Zhang, S.; Wang, J. Tetrahedron 2005, 61, 6546-6552
46. Wang, B.; Wu, X.-Y.; Wong, O. A.; Nettles, B.; Zhao, M. X.; Chen, D.; Shi, Y. J. Org. Chem. 2009, 74, 3986-3989