Synthesis 2014; 46(10): 1297-1302
DOI: 10.1055/s-0033-1338603
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Hydrogenation of Imines via Metal–Organo Cooperative Catalysis

Weijun Tang
a  Key Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. of China
,
Jianliang Xiao*
a  Key Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, P. R. of China
b  Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK   Fax: +44(151)7943588   Email: jxiao@liverpool.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 19 January 2014

Accepted after revision: 12 February 2014

Publication Date:
14 March 2014 (online)

Abstract

The combination of a chiral phosphoric acid with an iridium complex affords a catalyst that allows for highly enantioselective hydrogenation of imines. Mechanistic studies suggest that the hydrogenation proceeds through a ternary transition state at the ­hydride-transfer step, in which the organocatalyst interacts with both the hydride donor and acceptor.

 
  • References

    • 1a Spinder F, Blaser H.-U In Handbook of Homogeneous Hydrogenation . de Vries JG, Elsevier CJ. Wiley-VCH; Weinheim: 2007: 1193
    • 1b Breuer M, Ditrich K, Habicher T, Hauer B, Keßeler M, Stürmer R, Zelinski T. Angew. Chem. Int. Ed. 2004; 43: 788

      For recent reviews on asymmetric hydrogenation of imines, see:
    • 2a Nugent TC, El-Shazly M. Adv. Synth. Catal. 2010; 352: 753
    • 2b Xie JH, Zhu SF, Zhou QL. Chem. Rev. 2011; 111: 1713

    • For a significant industrial application, see:
    • 2c Blaser H.-U. Adv. Synth. Catal. 2002; 344: 17

      For recent examples of asymmetric hydrogenation of imines, see:
    • 3a Moessner C, Bolm C. Angew. Chem. Int. Ed. 2005; 44: 7564
    • 3b Yang Q, Shang G, Gao W, Deng J, Zhang X. Angew. Chem. Int. Ed. 2006; 45: 3832
    • 3c Zhu S, Xie J, Zhang Y, Li S, Zhou Q. J. Am. Chem. Soc. 2006; 128: 12886
    • 3d Reetz MT, Bondarev O. Angew. Chem. Int. Ed. 2007; 46: 4523
    • 3e Li C, Xiao J. J. Am. Chem. Soc. 2008; 130: 13208
    • 3f Mršić N, Minnaard AJ, Feringa BL, de Vries JG. J. Am. Chem. Soc. 2009; 131: 8358
    • 3g Han ZB, Wang Z, Zhang XM, Ding KL. Angew. Chem. Int. Ed. 2009; 48: 5345
    • 3h Hou G, Gosselin F, Li W, McWilliams C, Sun Y, Weisel M, O’Shea PD, Chen C, Davies IW, Zhang X, Alejandro B. J. Am. Chem. Soc. 2009; 131: 9882
    • 3i Hou G, Tao R, Sun Y, Zhang X, Gosselin F. J. Am. Chem. Soc. 2010; 132: 2124
    • 3j Baeza A, Pfaltz A. Chem. Eur. J. 2010; 16: 4003
    • 3k Zhou SL, Fleischer S, Junge K, Beller M. Angew. Chem. Int. Ed. 2011; 50: 5120
    • 3l Chen F, Wang TL, He YM, Ding ZY, Li ZW, Xu LJ, Fan QH. Chem. Eur. J. 2011; 17: 1109
    • 3m Zhou XY, Bao M, Zhou YG. Adv. Synth. Catal. 2011; 353: 84
    • 3n Chen F, Ding ZY, He YM, Qin J, Wang TL, Fan QH. Tetrahedron 2012; 68: 5248
    • 3o Hou CJ, Wang YH, Zheng Z, Xu J, Hu XP. Org. Lett. 2012; 14: 3554
    • 3p Arai N, Utsumi N, Matsumoto Y, Murata K, Tsutsumi K, Ohkuma T. Adv. Synth. Catal. 2012; 354: 2089
    • 3q Werkmeister S, Fleischer S, Junge K, Beller M. Chem. Asian J. 2012; 7: 2562
    • 3r Gao K, Wu B, Yu CB, Chen QA, Ye ZS, Zhou YG. Org. Lett. 2012; 14: 3890
    • 3s Schramm Y, Barrios-Landeros F, Pfaltz A. Chem. Sci. 2013; 4: 2760

      For recent reviews on organocatalytic transfer hydrogenation of imines, see:
    • 5a Kampen D, Reisinger CM, List BJ. Top. Curr. Chem. 2010; 291: 395
    • 5b Wang Z, Jiang Z. Asian J. Chem. 2010; 22: 4141
    • 5c Rueping M, Sugiono E, Schoepke FR. Synlett 2010; 852
    • 5d Zheng C, You SL. Chem. Soc. Rev. 2012; 41: 2498
    • 5e de Vries JG, Mršić N. Catal. Sci. Technol. 2011; 1: 727
    • 6a Hoffmann S, Seayad AM, List B. Angew. Chem. Int. Ed. 2005; 44: 7424
    • 6b Storer RI, Carrera DE, Ni Y, MacMillan DW. C. J. Am. Chem. Soc. 2006; 128: 84
    • 6c Wakchaure VN, Nicoletti M, Ratjen L, List BJ. Synlett 2010; 2708
    • 6d Wakchaure VN, Zhou J, Hoffmann S, List BJ. Angew. Chem. Int. Ed. 2010; 49: 4612
    • 6e Saito K, Akiyama T. Chem. Commun. 2012; 48: 4573 ; also see ref. 15

      For reviews, see:
    • 7a Shao ZH, Zhang HB. Chem. Soc. Rev. 2009; 38: 2745
    • 7b Zhong C, Shi X. Eur. J. Org. Chem. 2010; 2999
    • 7c Rueping M, Koenigs RM, Atodiresei J. Chem. Eur. J. 2010; 16: 9350
    • 7d Allen AE, MacMillan DW. C. Chem. Sci. 2012; 3: 633
    • 7e Stegbauer L, Sladojevich F, Dixon DJ. Chem. Sci. 2012; 3: 942
    • 7f Yu ZK, Jin WW, Jiang QB. Angew. Chem. Int. Ed. 2012; 51: 6060
    • 7g Du Z, Shao Z. Chem. Soc. Rev. 2013; 42: 1337
    • 8a Wang C, Li CQ, Wu XF, Pettman A, Xiao JL. Angew. Chem. Int. Ed. 2009; 48: 6524
    • 8b Wang C, Pettman A, Basca J, Xiao JL. Angew. Chem. Int. Ed. 2010; 49: 7948
    • 8c Wang C, Villa-Marcos B, Xiao JL. Chem. Commun. 2011; 47: 9773
    • 8d Tan J, Tang WJ, Sun Y, Jiang Z, Chen F, Xu L, Fan Q, Xiao JL. Tetrahedron 2011; 67: 6206
    • 8e Wu J, Wang C, Tang W, Pettman A, Xiao JL. Chem. Eur. J. 2012; 18: 9525
    • 8f Wu J, Tang WJ, Pettman A, Xiao JL. Adv. Synth. Catal. 2013; 355: 35
    • 8g Wu J, Barnard J, Zhang Y, Talwar D, Robertson C, Xiao JL. Chem. Commun. 2013; 49: 7052
    • 8h Tang WJ, Lau C, Wu X, Xiao JL. Synlett 2014; 25: 81
  • 9 Li C, Xiao JL. J. Am. Chem. Soc. 2008; 130: 13208

    • For some other examples of asymmetric reduction with iridium catalysts, see:
    • 10a Soltani O, Ariger MA, Carreira EM. Org. Lett. 2009; 11: 4196
    • 10b Soltani O, Ariger MA, Vázquez-Villa H, Carreira EM. Org. Lett. 2010; 12: 2893
    • 10c Ramadhar TR, Batey RA. Synthesis 2011; 1321
  • 11 Li CQ, Wang C, Villa-Marcos B, Xiao JL. J. Am. Chem. Soc. 2008; 130: 14450

    • For ionic hydrogenation mechanism, see:
    • 12a Bullock RM. Chem. Eur. J. 2004; 10: 2366
    • 12b Guan HR, Limura M, Magee MP, Norton JR, Zhu G. J. Am. Chem. Soc. 2005; 127: 7805
    • 13a Li CQ, Villa-Marcos B, Xiao JL. J. Am. Chem. Soc. 2009; 131: 6967
    • 13b Villa-Marcos B, Li CQ, Mulholland KR, Hogan PJ, Xiao JL. Molecules 2010; 15: 2453
  • 14 Zhang Y, Lim CS, Sim DS. B, Pan HJ, Zhao Y. Angew. Chem. Int. Ed. 2014; 53: 1399
    • 15a Li C. Ph.D. Thesis. University of Liverpool; UK: 2009
    • 15b Klussmann M. Angew. Chem. Int. Ed. 2009; 48: 7124
    • 16a Rueping M, Sugiono E, Azap C, Theissmann T, Bolte M. Org. Lett. 2005; 7: 3781
    • 16b Hoffmann S, Seayad AM, List B. Angew. Chem. Int. Ed. 2005; 44: 7424
  • 17 Rueping M, Koenigs RM. Chem. Commun. 2011; 47: 304
  • 18 Tang WJ, Johnston S, Li CQ, Iggo JA, Bacsa J, Xiao JL. Chem. Eur. J. 2013; 19: 14187
  • 19 Tang WJ, Johnston S, Iggo J, Berry NG, Phelan M, Lian L, Basca J, Xiao JL. Angew. Chem. Int. Ed. 2013; 52: 1668