Synthesis 2015; 47(04): 460-471
DOI: 10.1055/s-0034-1378939
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in the Development of Chiral Metal Catalysts for the Asymmetric Hydrogenation of Ketones

Jian-Hua Xie*, Deng-Hui Bao, Qi-Lin Zhou
  • State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China   Email: jhxie@nankai.edu.cn
Further Information

Publication History

Received: 07 October 2014

Accepted after revision: 03 November 2014

Publication Date:
21 November 2014 (eFirst)

Abstract

This review describes recent advances in the development of chiral metal catalysts for the asymmetric hydrogenation of ketones to give chiral alcohols, important building blocks for biologically active substances such as pharmaceuticals and natural products. Chiral ruthenium–diphosphine/diamine complexes have received intensive study and many efficient chiral ruthenium catalysts bearing chiral diphosphine and diamine ligands have been developed over the past few decades. In addition, chiral ruthenium, iridium, osmium, iron, copper, and palladium complexes with various chiral ligands have also emerged as highly efficient chiral metal catalysts for the asymmetric hydrogenation of ketones. A wide range of ketones are hydrogenated using these chiral metal catalysts to give chiral alcohols with excellent enantioselectivity with high turnover numbers (TONs) and turnover frequencies (TOFs).

1 Introduction

2 Chiral Ruthenium Catalysts

3 Chiral Iridium Catalysts

4 Other Chiral Metal Catalysts

5 Conclusion and Outlook

 
  • References

    • 1a Ohkuma T, Ooka H, Hashiguchi S, Ikariya T, Noyori R. J. Am. Chem. Soc. 1995; 117: 2675
    • 1b Noyori R. Angew. Chem. Int. Ed. 2002; 41: 2008
    • 2a Xie J.-H, Zhou Q.-L. Acta Chim. Sin. 2012; 70: 1427
    • 2b Zhao B, Han Z, Ding K. Angew. Chem. Int. Ed. 2013; 52: 4744
  • 3 Blaser H.-U, Spindler F, Thommen M In The Handbook of Homogeneous Hydrogenation . de Vries JG, Elsevier CJ. Wiley-VCH; Weinheim; 2007: 1279
  • 4 Burk MJ, Hems W, Herzberg D, Malan C, Zanotti-Gerosa A. Org. Lett. 2000; 2: 4173
    • 5a Wu J, Chen H, Kwok W.-H, Guo R.-W, Zhou Z.-Y, Yeung C.-H, Chan AS. C. J. Org. Chem. 2002; 67: 7908
    • 5b Wu J, Ji J.-X, Guo R.-W, Chan AS. C. Chem. Eur J. 2003; 9: 2963
    • 6a Xie J.-H, Wang L.-X, Fu Y, Zhu S.-F, Fan B.-M, Duan H.-F, Zhou Q.-L. J. Am. Chem. Soc. 2003; 125: 4404
    • 6b Xie J.-H, Liu S, Huo X.-H, Cheng X, Duan H.-F, Fan B.-M, Wang L.-X, Zhou Q.-L. J. Org. Chem. 2005; 70: 2967
    • 7a Liu S, Xie J.-H, Wang L.-X, Zhou Q.-L. Angew. Chem. Int. Ed. 2007; 46: 7506
    • 7b Xie J.-H, Liu S, Kong W.-L, Bai W.-J, Wang X.-C, Wang L.-X, Zhou Q.-L. J. Am. Chem. Soc. 2009; 131: 4222
    • 7c Liu S, Xie J.-H, Li W, Kong W.-L, Wang L.-X, Zhou Q.-L. Org. Lett. 2009; 11: 4994
    • 7d Bai W.-J, Xie J.-H, Li Y.-L, Liu S, Zhou Q.-L. Adv. Synth. Catal. 2010; 352: 81
    • 7e Liu C, Xie J.-H, Li Y.-L, Chen J.-Q, Zhou Q.-L. Angew. Chem. Int. Ed. 2013; 52: 593
    • 7f Xie J.-H, Zhou Q.-L. Acta Chim. Sin. 2014; 72: 778
  • 8 Henschke JP, Burk MJ, Malan CG, Herzberg D, Peterson JA, Wildsmith AJ, Cobley CJ, Casy G. Adv. Synth. Catal. 2003; 345: 300
    • 9a Hu A, Ngo HL, Lin W. Org. Lett. 2004; 6: 2937
    • 9b Ngo HL, Lin W. J. Org. Chem. 2005; 70: 1177
  • 10 Li W, Sun X, Zhou L, Hou G, Yu S, Zhang X. J. Org. Chem. 2009; 74: 1397
    • 11a Xu Y, Alcock NW, Clarkson GJ, Docherty G, Woodward G, Wills M. Org. Lett. 2004; 6: 4105
    • 11b Xu Y, Clarkson GC, Docherty G, North CL, Woodward G, Wills M. J. Org. Chem. 2005; 70: 8079
  • 12 Stegink B, van Boxtel L, Lefort L, Minnaard AJ, Feringa BL, de Vries JG. Adv. Synth. Catal. 2010; 352: 2621
  • 13 Jing Q, Zhang X, Sun J, Ding K. Adv. Synth. Catal. 2005; 347: 1193
    • 14a Mikami K, Wakabayashi K, Aikawa K. Org. Lett. 2006; 8: 1517
    • 14b Jing Q, Sandoval CA, Wang Z, Ding K. Eur. J. Org. Chem. 2006; 3606
  • 15 Rodríguez S, Qu B, Fandrick KR, Buono F, Haddad N, Xu Y, Herbage MA, Zeng X, Ma S, Grinberg M, Lee H, Han ZS, Yee NK, Senanayake CH. Adv. Synth. Catal. 2014; 356: 301
  • 16 Ohkuma T, Hattori T, Ooka H, Inoue T, Noyori R. Org. Lett. 2004; 6: 2681
  • 17 Arai N, Akashi M, Sugizaki S, Ooka H, Inoue T, Ohkuma T. Org. Lett. 2010; 12: 3380
  • 18 Grasa GA, Zanotti-Gerosa A, Medlock JA, Hems WP. Org. Lett. 2005; 7: 1449
    • 19a Sandoval CA, Ohkuma T, Muñiz K, Noyori R. J. Am. Chem. Soc. 2003; 125: 13490
    • 19b Abdur-Rashid K, Clapham SE, Hadzovic A, Harvey JN, Lough AJ, Morris RH. J. Am. Chem. Soc. 2002; 124: 15104
    • 19c Sandoval CA, Li Y, Ding K, Noyori R. Chem. Asian J. 2008; 3: 1801
  • 20 Genov DG, Ager DJ. Angew. Chem. Int. Ed. 2004; 43: 2816
  • 21 Ohkuma T, Sandoval CA, Srinivasan R, Lin Q, Wei Y, Muñiz K, Noyori R. J. Am. Chem. Soc. 2005; 127: 8288
  • 22 Arai N, Suzuki K, Sugizaki S, Sorimachi H, Ohkuma T. Angew. Chem. Int. Ed. 2008; 47: 1770
    • 23a Arai N, Ooka H, Azuma K, Yabuuchi T, Kurono N, Inoue T, Ohkuma T. Org. Lett. 2007; 9: 939
    • 23b Ooka H, Arai N, Azuma K, Kurono N, Ohkuma T. J. Org. Chem. 2008; 73: 9084
  • 24 Arai N, Azuma K, Nii N, Ohkuma T. Angew. Chem. Int. Ed. 2008; 47: 7457
  • 25 Li Y, Ding K, Sandoval CA. Org. Lett. 2009; 11: 907
  • 26 Li Y, Zhou Y, Shi Q, Ding K, Noyori R, Sandoval CA. Adv. Synth. Catal. 2011; 353: 495
  • 27 Zhu Q, Shi D, Xia C, Huang H. Chem. Eur. J. 2011; 17: 7760
  • 28 Chen X, Zhou H, Zhang K, Li J, Huang H. Org. Lett. 2014; 16: 3912
  • 29 Hu A, Ngo HL, Lin W. J. Am. Chem. Soc. 2003; 125: 11490
  • 30 Hu A, Yee GT, Lin W. J. Am. Chem. Soc. 2005; 127: 12486
  • 31 Liang Y, Jing Q, Li X, Shi L, Ding K. J. Am. Chem. Soc. 2005; 127: 7694
  • 32 Ohkuma T, Koizumi M, Muñiz K, Hilt G, Kabuto C, Noyori R. J. Am. Chem. Soc. 2002; 124: 6508
  • 33 Matsumura K, Arai N, Hori K, Saito T, Sayo N, Ohkuma T. J. Am. Chem. Soc. 2011; 133: 10696
    • 34a Haak K.-J, Hashiguchi S, Fujii A, Ikariya T, Noyori R. Angew. Chem., Int. Ed. Engl. 1997; 36: 285
    • 34b Noyori R, Hashiguchi S. Acc. Chem. Res. 1997; 30: 97
    • 34c Ikariya T, Murata K, Noyori R. Org. Biomol. Chem. 2006; 4: 393
  • 35 Ohkuma T, Utsumi N, Tsutsumi K, Murata K, Sandoval C, Noyori N. J. Am. Chem. Soc. 2006; 128: 8724
  • 36 Ohkuma T, Tsutsumi K, Utsumi N, Arai N, Noyori N. Org. Lett. 2007; 9: 255
  • 37 Ito M, Endo Y, Ikariya T. Organometallics 2008; 27: 6053
  • 38 Touge T, Hakamata T, Nara H, Kobayshi T, Sayo N, Saiyo T, Kayaki Y, Ikariya T. J. Am. Chem. Soc. 2011; 133: 14960
  • 39 Jolley KE, Zanotti-Gerosa A, Hancock F, Dyke A, Grainger DM, Medlock JA, Nedden HG, Le Paih JJ. M, Roseblade SJ, Seger A, Sivakumar V, Prokes I, Morris DJ, Wills M. Adv. Synth. Catal. 2012; 354: 2545
  • 40 Hedberg C, Källström K, Arvidsson PI, Brandt P, Andersson PG. J. Am. Chem. Soc. 2005; 127: 15083
  • 41 Naud F, Malan C, Spindler F, Rüggeberg C, Schmidt AT, Blaser H.-U. Adv. Synth. Catal. 2006; 348: 47
  • 42 Hansen KB, Chilenski JR, Desmond R, Devine PN, Grabowski EJ. J, Heid R, Kubryk M, Mathre DJ, Varsolona R. Tetrahedron: Asymmetry 2003; 14: 3581
  • 43 Schuecher R, Zirakzadeh A, Mereiter K, Spindler F, Weissensteiner W. Organometallics 2011; 30: 4711
    • 44a Guo H, Liu D, Butt NA, Liu Y, Zhang W. Tetrahedron 2012; 68: 3295
    • 44b Wang J, Liu D, Liu Y, Zhang W. Org. Biomol. Chem. 2013; 11: 3855
    • 45a Clarke ML, Diaz-Valenzuela MB, Slawin AM. Z. Organometallics 2007; 26: 16
    • 45b Diaz-Valenzuela MB, Philips SD, France MB, Gunn ME, Clarke ML. Chem. Eur J. 2009; 15: 1227
    • 45c Philips SD, Fuentes JA, Clarke ML. Chem. Eur J. 2010; 16: 8002
  • 46 Yamamura T, Nakatsuka H, Tanaka S, Kitamura M. Angew. Chem. Int. Ed. 2013; 52: 9313
  • 47 Ito J.-I, Ujiie S, Nishiyama H. Organometallics 2009; 28: 630
  • 48 Li W, Hou G, Wang C, Jiang Y, Zhang X. Chem. Commun. 2010; 46: 3979
  • 49 Baratta W, Ballico M, Chelucci G, Siega K, Rigo P. Angew. Chem. Int. Ed. 2007; 46: 7651
  • 50 Baratta W, Chelucci G, Magnolia S, Siega K, Rigo P. Chem. Eur J. 2009; 15: 726
  • 51 Baratta W, Fanfoni L, Magnolia S, Siega K, Rigo P. Eur. J. Inorg. Chem. 2010; 1419
  • 52 Huang H, Okuno T, Tsuda K, Yoshimura M, Kitamura M. J. Am. Chem. Soc. 2006; 128: 8716
  • 53 Patchett R, Magpantay I, Saudan L, Schotes C, Mezzetti A, Santoro F. Angew. Chem. Int. Ed. 2013; 52: 10352
  • 54 Roux EL, Malacea R, Manoury E, Poli R, Gonsalvi L, Peruzzini M. Adv. Synth. Catal. 2007; 349: 309
    • 55a Xie J.-B, Xie J.-H, Liu X.-Y, Kong W.-L, Li S, Zhou Q.-L. J. Am. Chem. Soc. 2010; 132: 4538
    • 55b Xie J.-B, Xie J.-H, Liu X.-Y, Zhang Q.-Q, Zhou Q.-L. Chem. Asian J. 2011; 6: 899
    • 56a Xie J.-H, Liu X.-Y, Xie J.-B, Wang L.-X, Zhou Q.-L. Angew. Chem. Int. Ed. 2011; 50: 7329
    • 56b Xie J.-H, Liu X.-Y, Yang X.-H, Xie J.-B, Wang L.-X, Zhou Q.-L. Angew. Chem. Int. Ed. 2012; 51: 201
    • 56c Zhang Q.-Q, Xie J.-H, Yang X.-H, Xie J.-B, Zhou Q.-L. Org. Lett. 2012; 14: 6158
  • 57 Yan P.-C, Zhu G.-L, Xie J.-H, Zhang X.-D, Zhou Q.-L, Li Y.-Q, Shen W.-H, Che D.-Q. Org. Process Res. Dev. 2013; 17: 307
  • 58 Qian J.-Q, Yan P.-C, Che D.-Q, Zhou Q.-L, Li Y.-Q. Tetrahedron Lett. 2014; 55: 1528
  • 59 Nie H, Zhou G, Wang Q, Chen W, Zhang S. Tetrahedron: Asymmetry 2014; 24: 1567
  • 60 Ohkuma T, Utsumi N, Watanabe M, Tsutsumi K, Arai N, Murata K. Org. Lett. 2007; 9: 2565
  • 61 Ito M, Endo Y, Tejima N, Ikariya T. Organometallics 2010; 29: 2397
  • 62 Irrgang T, Friedrich D, Kempe R. Angew. Chem. Int. Ed. 2011; 50: 2183
  • 63 Baratta W, Ballico M, Chelucci G, Siega K, Rigo P. Angew. Chem. Int. Ed. 2008; 47: 4362
  • 64 Baratta W, Barbato C, Magnalia S, Siega K, Rigo P. Chem. Eur J. 2010; 16: 3201
  • 65 Sui-Seng C, Freutel F, Lough AJ, Morris RH. Angew. Chem. Int. Ed. 2008; 47: 940
  • 66 Berkessel A, Reichau S, von der Höh A, Leconte N, Neudörfl JM. Organometallics 2011; 30: 3880
  • 67 Lagaditis PO, Sues PE, Sonnenberg JF, Wan KY, Lough AJ, Morris RH. J. Am. Chem. Soc. 2014; 136: 1367
  • 68 Li Y, Yu S, Wu X, Xiao J, Shen W, Dong Z, Gao J. J. Am. Chem. Soc. 2014; 136: 4031
  • 69 Shimizu H, Igarashi D, Kuriyama W, Yusa Y, Sayo N, Saito T. Org. Lett. 2007; 9: 1655
  • 70 Krabbe SW, Hatcher MA, Bowman RK, Mitchell MB, McClure MS, Johnson JS. Org. Lett. 2013; 15: 4560
  • 71 Zhou X.-Y, Wang D.-S, Bao M, Zhou Y.-G. Tetrahedron Lett. 2011; 52: 2826
  • 72 Arai N, Ohkuma T. Chem. Rec. 2012; 12: 284