Development of a chiral bis(guanidino)iminophosphorane as an uncharged organosuperbase for the enantioselective amination of ketones

Journal of the American Chemical Society

Volumn 135, Issue 41, 2013, Pages 15306-15309

  Takeda, Tadahiro ^b   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZODICARBOXYLATES; ENANTIOSELECTIVE; IMINOPHOSPHORANES; ORGANOCATALYSTS; ORGANOSUPERBASES;

CHEMICAL COMPOUNDS; KETONES; NUCLEOPHILES;

CATALYSTS;

BASE; BIS(GUANIDINO)IMINOPHOSPHORANE; KETONE; NUCLEOPHILE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 84886929518     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja408296h     Document Type: Article

References (33)

1. Palomo, C.; Oiarbide, M.; López, R. Chem. Soc. Rev. 2009, 38, 632
2. Superbases for Organic Synthesis; Ishikawa, T., Ed.; John Wiley & Sons: Chippenham, 2009; Chap. 4.
3. Ishikawa, T.; Kumamoto, T. Synthesis 2006, 737
4. Leow, D.; Tan, C.-H. Chem. Asian J. 2009, 4, 488
5. Sohtome, Y.; Nagasawa, K. Synlett 2010, 1
6. Leow, D.; Tan, C.-H. Synlett 2010, 1589
7. Terada, M. J. Synth. Org. Chem. Jpn. 2010, 68, 1159
8. Uraguchi, D.; Ooi, T. J. Synth. Org. Chem. Jpn. 2010, 68, 1185
9. Chinchilla, R.; Nájera, C.; Sánchez-Agulló, P. Tetrahedron: Asymmetry 1994, 5, 1393
10. Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157
11. Dong, S.; Liu, X.; Chen, X.; Mei, F.; Zhang, Y.; Gao, B.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2010, 132, 10560
12. Misaki, T.; Kawano, K.; Sugimura, T. J. Am. Chem. Soc. 2011, 133, 5695
13. Yang, Y.; Dong, S.; Liu, X.; Lin, L.; Feng, X. Chem. Commun. 2012, 48, 5040
14. Uraguchi, D.; Yoshida, K.; Ueki, Y.; Ooi, T. J. Am. Chem. Soc. 2012, 134, 19370
15. Wu, L.; Li, G.; Fu, Q.; Yu, L.; Tang, Z. Org. Biomol. Chem. 2013, 11, 443
16. Dai, Q.; Huang, H.; Zhao, J. C.-G. J. Org. Chem. 2013, 78, 4153
17. Zou, L.; Wang, B.; Mu, H.; Zhang, H.; Song, Y.; Qu, J. Org. Lett. 2013, 15, 3106
18. Uraguchi, D.; Ueki, Y.; Sugiyama, A.; Ooi, T. Chem. Sci. 2013, 4, 1308
19. Kondo, Y. In Superbases for Organic Synthesis; Ishikawa, T., Ed.; John Wiley & Sons: Chippenham, 2009; pp 145-185.
20. Schwesinger, R. Chimia 1985, 39, 269
21. Schwesinger, R.; Schlemper, H.; Hasenfratz, C.; Willaredt, J.; Dambacher, T.; Breuer, T.; Ottaway, C.; Fletschinger, M.; Boele, J.; Fritz, H.; Putzas, D.; Rotter, H. W.; Bordwell, F. G.; Satish, A. V.; Ji, G.-Z.; Peters, E.-M.; Peters, K.; von Schnering, H. G.; Walz, L. Liebigs Ann. 1996, 1055
22. Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. J. Org. Chem. 2005, 70, 1019
23. Kolomeitsev, A. A.; Koppel, I. A.; Rodima, T.; Barten, J.; Lork, E.; Röschenthaler, G.-V.; Kaljurand, I.; Kütt, A.; Koppel, I.; Mäemets, V.; Leito, I. J. Am. Chem. Soc. 2005, 127, 17656
24. Xu, X.; Yabuta, T.; Yuan, P.; Takemoto, Y. Synlett 2006, 137
25. Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128, 16044
26. Liu, T.-Y.; Cui, H.-L.; Zhang, Y.; Jiang, K.; Du, W.; He, Z.-Q.; Chen, Y.-C. Org. Lett. 2007, 9, 3671
27. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527
28. Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659
29. Konishi, H.; Lam, T. Y.; Malerich, J. P.; Rawal, V. H. Org. Lett. 2010, 12, 2028
30. Zhao, Y.; Pan, Y.; Liu, H.; Yang, Y.; Jiang, Z.; Tan, C.-H. Chem.-Eur. J. 2011, 17, 3571
31. Inokuma, T.; Furukawa, T.; Uno, T.; Suzuki, Y.; Yoshida, K.; Yano, Y.; Matsuzaki, K.; Takemoto, Y. Chem.-Eur. J. 2011, 17, 10470
32. Neutralization of 1 ·HX was conducted in accordance with Ooi's procedure, see: Uraguchi, D.; Sakaki, S.; Ooi, T. J. Am. Chem. Soc. 2007, 129, 12392
33. 31P NMR. See Supporting Information for details.