Asymmetric Hydrogenation of Heteroarenes with Multiple Heteroatoms

Abstract

Enantiopure heterocyclic architectures containing two or more heteroatoms in the ring system have attracted considerable attraction due to this motif playing a role of great importance in asymmetric synthesis and the pharmaceutical chemistry. This review focused on recent advances in the homogeneous asymmetric hydrogenation of heteroarenes with multiple heteroatoms, which provide an efficient and practical method to structural diverse chiral heterocyclic compounds.

1 Introduction

2 Asymmetric Hydrogenation of Five-Membered-Ring Hetero­arenes

2.1 Imidazoles and Oxazoles

2.2 Pyrazole Derivatives

2.3 Benzisoxazoles

3 Asymmetric Hydrogenation of Six-Membered-Ring Heteroarenes

3.1 Quinoxalines

3.2 Quinazolines

3.3 Pyrimidines

3.4 Pyrazines

4 Asymmetric Hydrogenation of Fused Nitrogen Heteroarenes

4.1 Heteroarenes Containing a Ring-Junction Nitrogen

4.2 Heteroarenes Containing a Fused Pyridine Ring

5 Conclusions and Outlook

Key words

hydrogenation - enantioselectivity - heteroarenes - heterocycles - asymmetric catalysis

• References

• 1a Kobayashi J, Morita H In The Alkaloids . Vol. 60. Cordell GA. Academic Press; New York: 2003: 165
• 1b Joule JA, Mills K In Heterocyclic Chemistry . 5th ed. John Wiley & Sons; Chichester: 2010: 97
• 2a Anton A, Baird BR In Kirk-Othmer Encyclopedia of Chemical Technology . 5th ed., Vol. 19 John Wiley & Sons; Chichester: 2006: 739
• 2b Jacobsen EN, Pfaltz A, Yamamoto H In Comprehensive Asymmetric Catalysis . Springer; Heidelberg: 2012
• 3a Tang W, Zhang X. Chem. Rev. 2003; 103: 3029
• 3b The Handbook of Homogeneous Hydrogenation . De Vries JG, Elsevier CJ. Wiley-VCH; Weinheim: 2007: 1
• 3c Roseblade SJ, Pfaltz A. Acc. Chem. Res. 2007; 40: 1402
• 3d Zhao B, Han Z, Ding K. Angew. Chem. Int. Ed. 2013; 52: 4744
• 3e Etayo P, Vidal-Ferran A. Chem. Soc. Rev. 2013; 42: 728
• 3f Chen Q.-A, Ye Z.-S, Duan Y, Zhou Y.-G. Chem. Soc. Rev. 2013; 42: 497
• 3g Yang X.-H, Xie J.-H, Zhou Q.-L. Org. Chem. Front. 2014; 1: 190
• 4a Church TL, Andersson PG. Coord. Chem. Rev. 2008; 252: 513
• 4b FleuryBrégeot N, de la Fuente V, Castillón S, Claver C. ChemCatChem 2010; 2: 1346
• 4c Xie J.-H, Zhu S.-F, Zhou Q.-L. Chem. Rev. 2011; 111: 1713
• 4d Woodmansee DH, Pfaltz A. Chem. Commun. 2011; 47: 7912
• 4e Wang C, Villa-Marcos B, Xiao J. Chem. Commun. 2011; 47: 9773
• 4f Hopmann KH, Bayer A. Coord. Chem. Rev. 2014; 268: 59
• 4g Xie J.-H, Bao D.-H, Zhou Q.-L. Synthesis 2015; 47: 460
• 5a Glorius F. Org. Biomol. Chem. 2005; 3: 4171
• 5b Lu S.-M, Han X.-W, Zhou Y.-G. Chin. J. Org. Chem. 2005; 25: 634
• 5c Zhou Y.-G. Acc. Chem. Res. 2007; 40: 1357
• 5d Kuwano R. Heterocycles 2008; 76: 909
• 5e Wang D.-W, Zhou Y.-G, Chen Q.-A, Wang D.-S In Chiral Amine Synthesis . Nugent TC. John Wiley; New York: 2010. Chap. 10, 299
• 5f Church TL, Andersson PG In Chiral Amine Synthesis . Nugent TC. John Wiley; New York: 2010. Chap. 6, 179
• 5g Lu S.-M, Zhou Y.-G In Science of Synthesis: Stereoselective Synthesis . Georg Thieme Verlag; Stuttgart: 2011. Chap. 1.6, 257
• 5h Rueping M, Dufour J, Schoepke FR. Green Chem. 2011; 13: 1084
• 5i Hu X.-P, Wang D.-S, Yu C.-B, Zhou Y.-G. Top. Organomet. Chem. 2011; 36: 313
• 5j Xie J, Zhou Q. Acta Chim. Sin. 2012; 70: 1427
• 5k Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
• 5l He Y.-M, Song F.-T, Fan Q.-H. Top. Curr. Chem. 2014; 343: 145

For selected reviews on the development of ligands for transition-metal catalysis, see ref. 3a and
• 6a Zhang W, Chi Y, Zhang X. Acc. Chem. Res. 2007; 40: 1278
• 6b Xie J.-H, Zhou Q.-L. Acc. Chem. Res. 2008; 41: 581
• 6c Zhou Q.-L In Privileged Chiral Ligands and Catalysts . Wiley-VCH; Weinheim: 2011: 1
• 6d Genet JP, Ayad T, Ratovelomanana-Vidal V. Chem. Rev. 2014; 114: 2824
• 7 Wang W.-B, Lu S.-M, Yang P.-Y, Han X.-W, Zhou Y.-G. J. Am. Chem. Soc. 2003; 125: 10536
• 8a Yu Z, Jin W, Jiang Q. Angew. Chem. Int. Ed. 2012; 51: 6060
• 8b Nagano T, Iimuro A, Yamaji K, Kita Y, Mashima K. Heterocycles 2014; 88: 103
• 8c Balakrishna B, Núñez-Rico JL, Vidal-Ferran A. Eur. J. Org. Chem. 2015; 5293
• 9 Kuwano R, Kameyama N, Ryuhei I. J. Am. Chem. Soc. 2011; 133: 7312
• 10a Low CM. R, Black JW, Broughton HB, Buck IM, Davies JM. R, Dunstone DJ, Hull RA. D, Kalindjian SB, McDonald IM, Pether MJ, Shankley NP, Steel KI. M. J. Med. Chem. 2000; 43: 3505
• 10b Gould E, Lebl T, Slawin AM. Z, Reid M, Smith AD. Tetrahedron 2010; 66: 8992
• 10c Ma G, Deng J, Sibi MP. Angew. Chem. Int. Ed. 2014; 53: 11818
• 11 Chen Z.-P, Chen M.-W, Shi L, Yu C.-B, Zhou Y.-G. Chem. Sci. 2015; 6: 3415
• 12 Ikeda R, Kuwano R. Molecules 2012; 17: 6901
• 13a Sikorski JA. J. Med. Chem. 2006; 49: 1
• 13b Borrok MJ, Kiessling LL. J. Am. Chem. Soc. 2007; 129: 12780
• 13c Fantin M, Marti M, Auberson YP, Morari M. J. Neurochem. 2007; 103: 2200
• 14 Murata S, Sugimoto T, Matsuura S. Heterocycles 1987; 26: 763
• 15 Bianchini C, Barabro P, Scapacci G. J. Organomet. Chem. 2001; 621: 26
• 16a Bianchini C, Barbaro P, Scapacci G, Farnetti E, Graziani M. Organometallics 1998; 17: 3308
• 16b Tang W, Xu L, Fan Q.-H, Wang J, Fan B, Zhou Z, Lam K, Chan AS. C. Angew. Chem. Int. Ed. 2009; 48: 9135
• 16c Mršić N, Jerphagnon T, Minnaard AJ, Feringa BL, de Vries JG. Adv. Synth. Catal. 2009; 351: 2549
• 16d Wang D.-S, Zhou Y.-G. Tetrahedron Lett. 2010; 51: 3014
• 16e Qiu L, Kwong FY, Wu J, Lam WH, Chan S, Yu W.-Y, Li Y.-M, Guo R, Zhou Z, Chan AS. C. J. Am. Chem. Soc. 2006; 128: 5955
• 16f Núñez-Rico JL, Fernández-Pérez H, Benet-Buchholz J, Vidal-Ferran A. Organometallics 2010; 29: 6627
• 16g Cartigny D, Nagano T, Ayad T, Genêt J.-P, Ohshima T, Mashima K, Ratovelomanana-Vidal V. Adv. Synth. Catal. 2010; 352: 1886
• 16h Cartigny D, Berhal F, Nagano T, Phansavath P, Ayad T, Genêt J.-P, Ohshima T, Mashima K, Ratovelomanana-Vidal V. J. Org. Chem. 2012; 77: 4544
• 16i Nagano T, Iimuro A, Schwenk R, Ohshima T, Kita Y, Togni A, Mashima K. Chem. Eur. J. 2012; 18: 11578
• 16j Wang D.-W, Wang D.-S, Chen Q.-A, Zhou Y.-G. Chem. Eur. J. 2010; 16: 1133
• 17a Qin J, Chen F, Ding Z, He Y.-M, Xu L, Fan Q.-H. Org. Lett. 2011; 13: 6568
• 17b Arai N, Saruwatari Y, Isobe K, Ohkuma T. Adv. Synth. Catal. 2013; 355: 2769
• 17c Cobley CJ, Henschke JP. Adv. Synth. Catal. 2003; 345: 195
• 17d Henschke JP, Burk MJ, Malan CG, Herzberg D, Peterson JA, Wildsmith AJ, Cobley CJ, Casy G. Adv. Synth. Catal. 2003; 345: 300
• 18 Rueping M, Tato F, Schoepke FR. Chem. Eur. J. 2010; 16: 2688
• 19 Chen Q.-A, Wang D.-S, Zhou Y.-G, Duan Y, Fan H.-J, Yang Y, Zhang Z. J. Am. Chem. Soc. 2011; 133: 6126
• 20 Chen Q.-A, Gao K, Duan Y, Ye Z.-S, Shi L, Yang Y, Zhou Y.-G. J. Am. Chem. Soc. 2012; 134: 2442
• 21 Fleischer S, Zhou S, Werkmeister S, Junge K, Beller M. Chem. Eur. J. 2013; 19: 4997
• 22a Welch GC, Juan RR. S, Masuda JD, Stephan DW. Science (Washington, D. C.) 2006; 314: 1124
• 22b Welch GC, Cabrera L, Chase PA, Hollinlk E, Masuda JD, Wei P, Stephan DW. Dalton Trans. 2007; 3407
• 22c Stephan DW, Erker G. Angew. Chem. Int. Ed. 2010; 49: 46
• 22d Stephan DW, Erker G. Top. Curr. Chem. 2013; 332: 85
• 22e Liu Y, Du H. Acta Chim. Sin. 2014; 72: 771
• 22f Shi L, Zhou Y.-G. ChemCatChem 2015; 7: 54
• 23 Zhang Z, Du H. Angew. Chem. Int. Ed. 2015; 54: 623
• 24a Gravier D, Dupin J.-P, Casadebaig F, Hou G, Boisseau M, Bernard H. Eur. J. Med. Chem. 1989; 24: 531
• 24b Rhim H, Lee YS, Park SJ, Chung BY, Lee JY. Bioorg. Med. Chem. Lett. 2005; 15: 283
• 24c Choi JY, Seo HN, Lee MJ, Park SJ, Park SJ, Jeon JY, Kang JH, Pae AN, Rhim H, Lee JY. Bioorg. Med. Chem. Lett. 2007; 17: 471
• 25 Kita Y, Higashida K, Yamaji K, Iimuro A, Mashima K. Chem. Commun. 2015; 51: 4380
• 26a Reyes F, Fernández R, Rodríguez A, Francesch A, Taboada S, Ávila C, Cuevas C. Tetrahedron 2008; 64: 5119
• 26b Pastor JM, Salvador M, Argandoña M, Bernal V, Reina-Bueno M, Csonka LN, Iborra JL, Vargas C, Nieto JJ, Cánovas M. Biotechnol. Adv. 2010; 28: 782
• 27 Kuwano R, Hashiguchi Y, Ikeda R, Ishizuka K. Angew. Chem. Int. Ed. 2015; 54: 2393
• 28a Scott JD, Williams RM. Chem. Rev. 2002; 102: 1669
• 28b Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
• 28c Vieth M, Siegel MG, Higgs RE, Watson IA, Robertson DH, Savin KA, Durst GL, Hipskind PA. J. Med. Chem. 2004; 47: 224
• 28d Shao B, Huang J, Sun Q, Valenzano KJ, Schmid L, Nolan S. Bioorg. Med. Chem. Lett. 2005; 15: 719
• 28e Nakamura D, Kakiuchi K, Koga K, Shirai R. Org. Lett. 2006; 8: 6139
• 29a Rossen K, Weissman SA, Sager J, Reamer RA, Askin D, Volante RP, Reider PJ. Tetrahedron Lett. 1995; 36: 6419
• 29b Pye PJ, Rossen K, Reamer RA, Tsou NN, Volante RP, Reider PJ. J. Am. Chem. Soc. 1997; 119: 6207
• 29c Rossen K, Pye PJ, DiMichele LM, Volante RP, Reider PJ. Tetrahedron Lett. 1998; 39: 6823
• 30a Kuwano R, Ito Y. J. Org. Chem. 1999; 64: 1232
• 30b Li Y, He Y, Chen F, Fan Q.-H. Chin. J. Chem. 2014; 32: 991
• 31a Fuchs R. EP 0803502, 1997
• 31b Fuchs R. US 5945534, 1999
• 32a Papeo G, Gómez-Zurita Frau MA, Borghi D, Varasi M. Tetrahedron Lett. 2005; 46: 8635
• 32b Al-Mourabit A, Zancanella MA, Tilvic S, Romo D. Nat. Prod. Rep. 2011; 28: 1229
• 33 Huang W.-X, Yu C.-B, Shi L, Zhou YG. Org. Lett. 2014; 16: 3324
• 34 Abarca B, Ballesteros R, Elmasnouy M. Tetrahedron 1999; 55: 12881
• 35 Ortega N, Tang D.-TD, Urban S, Zhao D, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 9500
• 36a Xu Z, Kozlowski MC. J. Org. Chem. 2002; 67: 3072
• 36b DiVirgilio ES, Dugan EC, Mulrooney CA, Kozlowski MC. Org. Lett. 2007; 9: 385
• 36c Mantlo NB, Escribano A. J. Med. Chem. 2014; 57: 1
• 37 Zhang J, Chen F, He Y.-M, Fan Q.-H. Angew. Chem. Int. Ed. 2015; 54: 4622
• 38 Metallinos C, Barrett FB, Xu S. Synlett 2008; 720
• 39 Wang T, Chen F, Qin J, He Y.-M, Fan Q.-H. Angew. Chem. Int. Ed. 2013; 52: 7172