Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters

Organic Letters

Volumn 16, Issue 7, 2014, Pages 1948-1951

  Curto, John M ^a   Dickstein, Joshua S ^a   Berritt, Simon ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOXYLIC ACID; DRUG DERIVATIVE; ESTER; IMINE; PROLINE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; AMINO ACIDS; CARBOXYLIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; ESTERS; IMINES; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 84898732102     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500506t     Document Type: Article

References (47)

1. Xie, W.; Zou, B.; Pei, D.; Ma, D. Org. Lett. 2005, 7, 2775
2. Savage, S. A.; Waltermire, R. E.; Campagna, S.; Bordawekar, S.; Toma, J. D. R. Org. Process Res. Dev. 2009, 13, 510
3. Washburn, W. N. Bioorg. Med. Chem. Lett. 2004, 14, 3525
4. Ma, D. W.; Tian, H. Q.; Zou, G. X. J. Org. Chem. 1999, 64, 120
5. Stilz, H. U.; Jablonka, B.; Knolle, J.; Paulus, E. F.; Zoller, G. J. Med. Chem. 1996, 39, 2118
6. Graver, A.; Konig, B. Eur. J. Org. Chem. 2009, 30, 5099
7. Venkatraman, J.; Shankaramma, S. C.; Balaram, P. Chem. Rev. 2001, 101, 3131
8. Liu, Z.; Mehta, S. J.; Hruby, V. J. Organic Preparations and Procedures International: The New Journal for Organic Synthesis 2012, 44, 222
9. Cativiela, C.; Diaz-De-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569
10. Vogt, H.; Brase, S. Org. Biomol. Chem. 2007, 5, 406
11. Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228
12. Ooi, T.; Takeuchi, M.; Ohara, D.; Maruoka, K. Synlett 2001, 7, 1185
13. Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686
14. Application of ref 5b utilizing an analog of phenylglycine gave a 35% yield and 45% ee; see: Metro, T.-X.; Cochi, A.; Pardo, D. G.; Cossy, J. J. Org. Chem. 2011, 76, 2594
15. Wang, J.; Liu, X.; Feng, X. Chem. Rev. 2011, 111, 6947
16. Wieland, L. C.; Vieira, E. M.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 570
17. Fu, P.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 5530
18. Basra, S.; Fennie, M. W.; Kozlowski, M. C. Org. Lett. 2006, 8, 2659
19. Zhuang, W.; Saaby, S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 4476
20. Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873-888
21. Maruoka, K. Org. Process Res. Dev. 2008, 12, 679
22. Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635
23. Chen, W.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2068
24. Fiaud, J. C.; Kagan, H. Tetrahedron Lett. 1970, 11, 1813
25. Mizota, I.; Matsuda, Y.; Kamimura, S.; Tanaka, H.; Shimizu, M. Org. Lett. 2013, 15, 4206
26. Shimizu, M.; Kurita, D.; Mizota, I. Asian J. Org. Chem. 2013, 2, 208
27. Shimizu, M.; Takao, Y.; Katsurayama, H.; Mizota, I. Asian J. Org. Chem. 2013, 2, 130
28. Mizota, I.; Tanaka, K.; Shimizu, M. Tetrahedron Lett. 2012, 53, 1847
29. Niwa, Y.; Shimizu, M. J. Am. Chem. Soc. 2003, 125, 3720
30. Niwa, Y.; Takayama, K.; Shimizu, M. Bull. Chem. Soc. Jpn. 2002, 75, 1819
31. Shimizu, M.; Niwa, Y. Tetrahedron Lett. 2001, 42, 2829
32. Dickstein, J. S.; Fennie, M. W.; Norman, A. L.; Paulose, B. J.; Kozlowski, M. C. J. Am. Chem. Soc. 2008, 130, 15794
33. Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. J. Am. Chem. Soc. 2008, 130, 9257
34. Metz, A. E.; Berritt, S.; Dreher, S. D.; Kozlowski, M. C. Org. Lett. 2012, 3, 760
35. Dickstein, J. S.; Kozlowski, M. C. Chem. Soc. Rev. 2008, 37, 1166
36. Meyers, A. I.; Knaus, G.; Kamata, K.; Ford, M. E. J. Am. Chem. Soc. 1976, 98, 567
37. Di Noto, V.; Bandoli, G.; Dolmella, A.; Zarli, B.; Vivani, M.; Vidali, M. J. Chem. Cryst. 1995, 25, 375
38. Allan, J. F.; Clegg, W.; Henderson, K. W.; Horsburgh, L.; Kennedy, A. R. J. Organomet. Chem. 1998, 559, 173
39. Williard, P. G.; Salvino, J. M. J. Chem. Soc., Chem. Commun. 1986, 153
40. Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.; Nishida, A. J. Org. Chem. 2006, 71, 4255
41. Nelson, S. G.; Bungard, C. J.; Wang, K. J. Am. Chem. Soc. 2003, 125, 13000
42. Erdogan, G.; Grotjahn, D. B. J. Am. Chem. Soc. 2009, 131, 10354
43. Larsen, C. R.; Grotjahn, D. B. J. Am. Chem. Soc. 2012, 134, 10357
44. Park, K. H.; Kurth, M. J. Tetrahedron 2002, 58, 8629
45. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390
46. Cativiela, C.; Ordonez, M. Tetrahedron: Asymmetry 2009, 20, 1
47. Cativiela, C.; Diaz-De-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645