Diastereoselective control of intramolecular aza-Michael reactions using achiral catalysts

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5556-5559

  Zhong, Cheng ^a,b   Wang, Yikai ^a,b   Hung, Alvin W ^a,b   Schreiber, Stuart L ^a,b   Young, Damian W ^a,b  

^a BROAD INSTITUTE OF MIT AND HARVARD   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; KETONE; PALLADIUM;

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

AZA COMPOUNDS; CARBAMATES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 80054679491     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202276h     Document Type: Article

References (40)

1. Spiegel, D. A.; Schroeder, F. C.; Duvall, J. R.; Schreiber, S. L. J. Am. Chem. Soc. 2006, 128, 14766
2. Marcaurelle, L. A.; Comer, E.; Dandapani, S.; Duvall, J. R.; Gerard, B.; Kesavan, S.; Lee, M. D., IV; Liu, H.; Lowe, J. T.; Marie, J.-C.; Mulrooney, C. A.; Pandya, B. A.; Rowley, A.; Ryba, T. D.; Suh, B.-C.; Wei, J.; Young, D. W.; Akella, L. B.; Ross, N. T.; Zhang, Y.-L.; Fass, D. M.; Reis, S. A.; Zhao, W.-N.; Haggarty, S. J.; Palmer, M.; Foley, M. A. J. Am. Chem. Soc. 2010, 132, 16962
3. Hung, A. W.; Ramek, A.; Wang, Y.; Kaya, T.; Wilson, J. A.; Clemons, P. A.; Young, D. W. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6799
4. Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard., G. S. J. Am. Chem. Soc. 1990, 112, 866
5. Potuzak, J. S.; Moilanen, S. B.; Tan., D. S. J. Am. Chem. Soc. 2005, 127, 13796
6. Balskus, E. P.; Jacobsen., E. N. Science. 2007, 317, 1736
7. Guo, H.; Dong, C.-G.; Kim, D.-S.; Urabe, D.; Wang, J.; Kim, J. T.; Liu, X.; Sasaki, T.; Kishi., Y. J. Am. Chem. Soc. 2009, 131, 15387
8. Xu, L.-W.; Xia, C.-G. Eur. J. Org. Chem. 2005, 633
9. Enders, D.; Wang, C.; Liebich, J. X. Chem.-Eur. J. 2009, 15, 11058
10. Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
11. Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991
12. Cardillo, G.; Tomassini, C. Chem. Soc. Rev. 1996, 117
13. Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328
14. Lu, X.; Deng, L. Angew. Chem., Int. Ed. 2008, 47, 7710
15. Cai, Q.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 8666
16. Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959
17. Palomo, C.; Oiarbide, M.; Halder, R.; Kelso, M.; Gómez-Bengoa, E.; García, J. M. J. Am. Chem. Soc. 2004, 126, 9188
18. Takasu, K.; Maiti, S.; Ihara, M. Heterocycles 2003, 59, 51
19. Bandini, M.; Eichholzer, A.; Tragni, M.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2008, 47, 3238
20. Rolfe, A.; Young, K.; Hanson, P. R. Eur. J. Org. Chem. 2008, 5254
21. For the most recent example, see: Ying, Y.; Kim, H.; Hong, J. Org. Lett. 2011, 13, 796
22. For review, see: Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. 1985, 24, 1
23. Fustero, S.; Jiménez, D.; Sánchez-Roselló, M.; del Pozo, C. J. Am. Chem. Soc. 2007, 129, 6700
24. Fustero, S.; Jiménez, D.; Moscardó, J.; Catalán, S.; del Pozo, C. Org. Lett. 2007, 9, 5283
25. Sudhakar, N.; Srinivasulu, G.; Rao, G. S.; Rao., B. V. Tetrahedron: Asymmetry 2008, 19, 2153
26. Gaunt, M. J.; Spencer, J. B. Org. Lett. 2001, 3, 25
27. Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 3, 1319
28. Reiter, M.; Turner, H.; Gouverneur, V. Chem.-Eur. J. 2006, 12, 7190
29. Ozawa, F.; Yoshifuji, M. Dalton Trans. 2006, 4987
30. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932
31. Trost, B. M.; Fandrick, D. R.; Dinh, D. C. J. Am. Chem. Soc. 2005, 127, 14186
32. For a review, see: Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1
33. For example, see: Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336
34. Wabnitz, T. C.; Yu, J. Q.; Spencer, J. B. Chem.-Eur. J. 2004, 10, 484
35. Wabnitz, T. C.; Spencer, J. B. Org. Lett. 2003, 5, 2141
36. Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986
37. Garcia-Garcia, P.; Lay, F.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2009, 48, 4363
38. Cheon, C. H.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 9246
39. Clemons, P. A.; Bodycombe, N. E.; Carrinski, H. A.; Wilson, J. A.; Shamji, A. F.; Wagner, B. K.; Koehler, A. N.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 18787
40. Chen, Y.; Zhong, C.; Petersen, J. L.; Akhmedov, N. G.; Shi, X. Org. Lett. 2009, 11, 2333