Synthesis 2015; 47(12): 1775-1779
DOI: 10.1055/s-0034-1380147
paper
© Georg Thieme Verlag Stuttgart · New York

An Unsymmetrical Iron Catalyst for the Asymmetric Transfer Hydrogenation­ of Ketones

Samantha A. M. Smith
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada   Email: robert.morris@utoronto.ca
,
Robert H. Morris*
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada   Email: robert.morris@utoronto.ca
› Author Affiliations
Further Information

Publication History

Received: 12 December 2014

Accepted: 14 January 2015

Publication Date:
20 February 2015 (online)


Abstract

A new iron(II)(Ph2P–NH–N–PCy2) complex with a dicyclohexylphosphino group trans to the NH group was found to catalyze the asymmetric transfer hydrogenation of a variety of ketones with high enantioselectivity.

Supporting Information

 
  • References

    • 1a Knowles WS, Noyori R. Acc. Chem. Res. 2007; 40: 1238
    • 1b Dupau P. Top. Organomet. Chem. 2012; 42: 47
    • 1c Saudan LA. Acc. Chem. Res. 2007; 40: 1309
    • 1d Noyori R. Adv. Synth. Catal. 2003; 345: 15
    • 1e Noyori R, Ohkuma T. Angew. Chem. Int. Ed. 2001; 40: 40
  • 2 Morris RH. Chem. Soc. Rev. 2009; 38: 2282
    • 3a Chen JS, Chen LL, Xing Y, Chen G, Shen WY, Dong ZR, Li YY, Gao JX. Acta Chim. Sin. 2004; 62: 1745
    • 3b Sui-Seng C, Freutel F, Lough AJ, Morris RH. Angew. Chem. Int. Ed. 2008; 47: 940
    • 3c Mikhailine AA, Lough AJ, Morris RH. J. Am. Chem. Soc. 2009; 131: 1394
    • 3d Meyer N, Lough AJ, Morris RH. Chem. Eur. J. 2009; 15: 5605
    • 3e Zhou S, Fleischer S, Junge K, Das S, Addis D, Beller M. Angew. Chem. Int. Ed. 2010; 49: 8121
    • 3f Lagaditis PO, Lough AJ, Morris RH. J. Am. Chem. Soc. 2011; 133: 9662
    • 3g Sues PE, Lough AJ, Morris RH. Organometallics 2011; 30: 4418
    • 3h Yu S, Shen W, Li Y, Dong Z, Xu Y, Li Q, Zhang J, Gao J. Adv. Synth. Catal. 2012; 354: 818
    • 3i Mikhailine AA, Maishan MI, Lough AJ, Morris RH. J. Am. Chem. Soc. 2012; 134: 12266
    • 3j Mikhailine AA, Maishan MI, Morris RH. Org. Lett. 2012; 14: 4638
    • 3k Prokopchuk DE, Morris RH. Organometallics 2012; 31: 7375
    • 3l Sonnenberg JF, Coombs N, Dube PA, Morris RH. J. Am. Chem. Soc. 2012; 134: 5893
    • 3m Zuo W, Li Y, Lough AJ, Morris RH. Science 2013; 342: 1080
    • 3n Sues PE, Demmans KZ, Morris RH. Dalton Trans. 2014; 43: 7650
    • 4a Berkessel A, Reichau S, von der Hoh A, Leconte N, Neudorfl JM. Organometallics 2011; 30: 3880
    • 4b Fleischer S, Werkmeister S, Zhou SL, Junge K, Beller M. Chem. Eur. J. 2012; 18: 9005
    • 4c Fleischer S, Zhou SL, Werkmeister S, Junge K, Beller M. Chem. Eur. J. 2013; 19: 4997
    • 4d Li Y, Yu S, Wu X, Xiao J, Shen W, Dong Z, Gao J. J. Am. Chem. Soc. 2014; 136: 4031
    • 4e Lagaditis PO, Sues PE, Sonnenberg JF, Wan KY, Lough AJ, Morris RH. J. Am. Chem. Soc. 2014; 136: 1367
    • 4f Zuo W, Tauer S, Prokopchuk DE, Morris RH. Organometallics 2014; 33: 5791
  • 5 Xu Y, Docherty GF, Woodward G, Wills M. Tetrahedron: Asymmetry 2006; 17: 2925
  • 6 Brands KM. J, Payack JF, Rosen JD, Nelson TD, Candelario A, Huffman MA, Zhao MM, Li J, Craig B, Song ZJ, Tschaen DM, Hansen K, Devine PN, Pye PJ, Rossen K, Dormer PG, Reamer RA, Welch CJ, Mathre DJ, Tsou NN, McNamara JM, Reider PJ. J. Am. Chem. Soc. 2003; 125: 2129