LOGIN TO YOUR ACCOUNT

Username
Password
Remember Me
Or use your Academic/Social account:

CREATE AN ACCOUNT

Or use your Academic/Social account:

Congratulations!

You have just completed your registration at OpenAire.

Before you can login to the site, you will need to activate your account. An e-mail will be sent to you with the proper instructions.

Important!

Please note that this site is currently undergoing Beta testing.
Any new content you create is not guaranteed to be present to the final version of the site upon release.

Thank you for your patience,
OpenAire Dev Team.

Close This Message

CREATE AN ACCOUNT

Name:
Username:
Password:
Verify Password:
E-mail:
Verify E-mail:
*All Fields Are Required.
Please Verify You Are Human:
fbtwitterlinkedinvimeoflicker grey 14rssslideshare1
Publisher: American Chemical Society
Languages: English
Types: Article
Subjects: QD
Identifiers:doi:10.1021/ol302354z
The synthesis of a series of tridentate ligands based on a homochiral 1,2-diamine structure attached to a triazole group and their subsequent applications to the asymmetric transfer hydrogenation of ketones are described. In the best cases, alcohols of up to 93% ee were obtained. Although base is not required, the use of Ru3(CO)12 as metal source is essential, indicating a unique mechanism for the formation of the active catalyst.
  • The results below are discovered through our pilot algorithms. Let us know how we are doing!

    • (1) (a) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300- 1308. (b) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393-406. (c) Gladiali, S. Alberico, E. Chem. Soc. Rev. 2006, 36, 226- 236. (d) Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201-2237.
    • (2) (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562-7563; (b) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521- 2522. (c) Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem. Int. Ed. 1997, 36, 285-288 (d) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739. (e) Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998-2001. (f) Wang, C.; Wu, X. F.; Xiao, J. L. Chem. Asian J. 2008, 3, 1750-1770. (g) Handgraaf, J.-W.; Meijer, E. J. J. Am. Chem. Soc. 2007, 129, 3099-3103. (h) Soni, R.; Cheung, F. K.; Clarkson, G. C.; Martins, J. E. D.; Graham, M. A.; Wills, M. Org. Biomol. Chem. 2011, 9, 3290- 3294.
    • (3) (a) Wills, M. in Modern Reduction Methods, ed. Andersson, P. G.; Munslow, I. J. Wiley-VCH, Weinheim, 2008, Chapter 11, pp 271- 296. (b) Uematsu, U.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916-4917. (c) Blacker, J.; Martin, J. Scale up studies in Asymmetric Transfer Hydrogenation. In Asymmetric Catalysis on an Industrial Scale: Challenges, Approaches and Solutions; ed Blaser H. U.; Schmidt, E. Wiley, 2004, 201-216. (d) Sun, X.; Manos, G.; Blacker, A. J.; Martin, J.; Gavriilidis, A. Org. Proc. Res. Dev. 2004, 8, 909-914. (e) Williams, G. D.; Wade, C. E.; M. Wills, M. Chem. Commun. 2005, 4735-4737.
    • (4) (a) Timmis, F.; Adolfsson, H. Org. Biomol. Chem. 2010, 8, 4536- 4539. (b) Cambreiro, X. C.; Pericas, M. A. Adv. Synth. Catal. 2011, 353, 113-124. (c) Evans, D. A.; Nelson, S. G.; Gagne M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800-9801. (d) Jiang, Y.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1998, 120, 3817-3818. (e) Yutong, J.; Qiongzhong, J.; Guoxin Z.; Xumu, Z. Tetrahedron Lett. 1997, 38, 6565- 6568. (f) Bøgevig, A.; Pastor, I. M.; Adolfsson, H. Chem. Eur. J. 2004, 10, 294-302. (g) Zaitsev, A. B.; Adolfsson, H. Org. Lett. 2006, 8, 5129- 5132. (h) Diaz-Valenzuela, M. B.; Phillips, S. D.; France, M. B.; Gunn, M. E.; Clarke, M. L. Chem; Eur. J. 2009, 15, 1227-1232. (i) Baratta, W.; Benedetti, F.; Del Zotto, A.; Fanfoni, L.; Felluga, F.; Magnolia, S.; Putignano, E.; Rigo, P. Organometallics 2010, 29, 3563-3570.
    • (5) (a) Struthers, H.; Mindt, T. L.; Schibli, R. Dalton Trans. 2010, 39, 675-696. (b) Rodionov, V. O.; Presolski, S. I.; Gardinier, S.; Lim, Y.-H.; Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12696-12704. (c) Liu, D.; Gao, W.; Dai, Q.; Zhang, X. Org. Lett. 2005, 7, 4907-4910 (d) Detz, R. J.; Heras, S. A. V.; de Gelder, R.; van Leeuwen, P. W. N. M.; Hiemstra, H.; Reek. J. N. H.; van Maarseveen, J. H. Org. Lett. 2006, 8, 3227-3230.
    • (6) (a) Gao, J.-X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087-1089. (b) Sues, P. E.; Lough, A. J.; Morris, R. H. Organometallics 2011, 30, 4418-4431. (c) Sonnenberg, J. F.; Coombs, N.; Dube, P. A.; Morris, R. H. J. Am. Chem. Soc. 2012, 134, 5893-5899. (d) Lagaditis, P. O.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2011, 133, 9662- 9665. (e) Morris, R. H. Chem. Soc. Rev. 2009, 8, 2282-2291.
    • (7) (a) Hayes, A. M.; Morris, D. J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2005, 127, 7318-7319; (b) Cheung, F. K.; Lin, C.; Minissi, F.; A. Lorente Crivillé, A.; Graham, M. A.; Fox, D. J.; Wills, M. Org. Lett. 2007, 9, 4659-4662. (c) Cheung, F. K.; Clarke, A. J.; Glarkson, G. J.; Fox, D. J.; Graham, M. A.; Lin, C.; Lorente Crivillé, A.; Wills, M. Dalton Trans. 2010, 39, 1395-1402. (d) Soni, R.; Collinson, J.-M.; Clarkson, G. C.; Wills, M. Org. Lett. 2011, 13, 4304-4307.
  • No related research data.
  • No similar publications.

Share - Bookmark

Cite this article