Catalytic Enantioselective Friedel–Crafts Reactions of Naphthols and Electron-Rich Phenols

Abstract

The enantioselective Friedel–Crafts reaction is a powerful tool for the construction of benzylic stereocenters in a stereodefined manner. Significant advances have already been achieved with heteroarenes such as indoles and pyrroles; however, the reaction with homoarenes is less developed. This short review covers the most relevant literature on enantioselective Friedel–Crafts reactions with naphthols and phenols.

1 Introduction

2 Friedel–Crafts Reactions Involving 1,2-Nucleophilic Addition to C=X Bonds

3 Friedel–Crafts Reactions Involving Conjugate Nucleophilic Addition to Electrophilic C=C Bonds

4 Friedel–Crafts Reactions Involving π-Allylic Complexes as Electrophiles

5 ipso-Friedel–Crafts Reactions

6 Conclusions

Key words

Friedel–Crafts reactions - asymmetric catalysis - hydroxyarenes - ketones - imines - nitroalkenes - unsaturated carbonyl compounds - allylation

• References

• 1a Bandini M, Umani-Ronchi A. Catalytic Asymmetric Friedel-Crafts Alkylations . John Wiley & Sons; Weinheim: 2016
• 1b Mortier J. Arene Chemistry . John Wiley & Sons; Hoboken: 2016
• 2 Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9608
• 3 Erker G, van der Zeijden AA. H. Angew. Chem. Int. Ed. 1990; 29: 512
• 4 Zhao J.-L, Liu L, Gu C.-L, Wang D, Chen Y.-J. Tetrahedron Lett. 2008; 49: 1476
• 5 Ren H, Wang P, Wang L, Tang Y. Org. Lett. 2015; 17: 4886
• 6 Vetica F, de Figueiredo RM, Cupioli E, Gambacorta A, Loreto MA, Miceli M, Gasperi T. Tetrahedron Lett. 2016; 57: 750
• 7 Montesinos-Magraner M, Vila C, Blay G, Fernández I, Muñoz MC, Pedro JR. Adv. Synth. Catal. 2015; 357: 3047
• 8 Wu D, Zhang X, Xu Y, Xue Y, Li J, Wang W, Zhu J. Asian J. Org. Chem. 2014; 3: 480
• 9 Kaur J, Kumar A, Chimni SS. Tetrahedron Lett. 2014; 55: 2138
• 10a Kumar A, Kaur J, Chauhan P, Chimni SS. Chem. Asian J. 2014; 9: 1305
• 10b Kaur J, Kumar A, Chimni SS. RSC Adv. 2014; 4: 62367
• 11 Qin L, Wang P, Zhang Y, Ren Z, Zhang X, Da C.-S. Synlett 2016; 27: 571
• 12 Niu L.-F, Xin Y.-C, Wang R.-L, Jiang F, Xu P.-F, Hui X.-P. Synlett 2010; 765
• 13 Chauhan P, Chimni SS. Eur. J. Org. Chem. 2011; 1636
• 14 Liu G, Zhang S, Li H, Zhang T, Wang W. Org. Lett. 2011; 13: 828
• 15 Takizawa S, Hirata S, Murai K, Fujioka H, Sasai H. Org. Biomol. Chem. 2014; 12: 5827
• 16 Li G.-X, Qu J. Chem. Commun. 2012; 48: 5518
• 17 Chauhan P, Chimni SS. Tetrahedron Lett. 2013; 54: 4613
• 18 Kato M, Hirao S, Nakano K, Sato M, Yamanaka M, Sohtome Y, Nagasawa K. Chem. Eur. J. 2015; 21: 18606
• 19 Montesinos-Magraner M, Cantón R, Vila C, Blay G, Fernández I, Muñoz MC, Pedro JR. RSC Adv. 2015; 5: 60101
• 20 Montesinos-Magraner M, Vila C, Cantón R, Blay G, Fernández I, Muñoz MC, Pedro JR. Angew. Chem. Int. Ed. 2015; 54: 6320
• 21 Kumari P, Barik S, Khan NH, Ganguly B, Kureshy RI, Abdi SH. R, Bajaj HC. RSC Adv. 2015; 5: 69493
• 22 Zhou D, Huang Z, Yu X, Wang Y, Li J, Wang W, Xie H. Org. Lett. 2015; 17: 5554
• 23 Takizawa S, Arteaga F, Yoshida Y, Kodera J, Nagata Y, Sasai H. Dalton Trans. 2013; 42: 11787
• 24 Kumari P, Jakhar A, Khan NH, Tak R, Kureshy RI, Abdi SH. R, Bajaj HC. Catal. Commun. 2015; 69: 138
• 25 Bai S, Liao Y, Lin L, Luo W, Liu X, Feng X. J. Org. Chem. 2014; 79: 10662
• 26 Liu T.-Y, Cui H.-L, Chai Q, Long J, Li B.-J, Wu Y, Ding L.-S, Chen Y.-C. Chem. Commun. 2007; 2228
• 27 Zhang H, Liao Y.-H, Yuan W.-C, Zhang X.-M. Eur. J. Org. Chem. 2010; 3215
• 28 Sohtome Y, Shin B, Horitsugi N, Takagi R, Noguchi K, Nagasawa K. Angew. Chem. Int. Ed. 2010; 49: 7299
• 29 Sohtome Y, Yamaguchi T, Shin B, Nagasawa K. Chem. Lett. 2011; 40: 843
• 30 Jarava-Barrera C, Esteban F, Navarro-Ranninger C, Parra A, Alemán J. Chem. Commun. 2013; 49: 2001
• 31 Hong L, Wang L, Sun W, Wong K, Wang R. J. Org. Chem. 2009; 74: 6881
• 32 Poulsen PH, Feu KS, Paz BM, Jensen F, Jørgensen KA. Angew. Chem. Int. Ed. 2015; 54: 8203
• 33 Paradisi E, Righi P, Mazzanti A, Ranieri S, Bencivenni G. Chem. Commun. 2012; 48: 11178
• 34 Saha S, Alamsetti SK, Schneider C. Chem. Commun. 2015; 51: 1461
• 35 Chen Y.-H, Cheng D.-J, Zhang J, Wang Y, Liu X.-Y, Tan B. J. Am. Chem. Soc. 2015; 137: 15062
• 36 Wang X.-S, Zheng C.-W, Zhao S.-L, Chai Z, Zhao G, Yang G.-S. Tetrahedron: Asymmetry 2008; 19: 2699
• 37 Takemoto Y. Chem. Pharm. Bull. 2010; 593
• 38 Jiang X, Wu L, Xing Y, Wang L, Wang S, Chen Z, Wang R. Chem. Commun. 2012; 48: 446
• 39 Lee HA, Kim DY. Bull. Korean Chem. Soc. 2013; 34: 3539
• 40 Lv J, Li X, Zhong L, Luo S, Cheng J.-P. Org. Lett. 2010; 12: 1096
• 41a Bai S, Liu X, Wang Z, Cao W, Lin L, Feng X. Adv. Synth. Catal. 2012; 354: 2096
• 41b Liu X, Lin L, Feng X. Acc. Chem. Res. 2011; 44: 574
• 42 Wang J.-Y, Zhang H, Liao YH, Yuan W.-C, Feng Y.-J, Zhang X.-M. Synlett 2012; 23: 796
• 43a Kaeobamrung J, Mahatthananchai J, Zheng P, Bode JW. J. Am. Chem. Soc. 2010; 132: 8810
• 43b Mahatthananchai J, Kaeobamrung J, Bode JW. ACS Catal. 2012; 2: 494
• 43c Li G.-T, Gu Q, You S.-L. Chem. Sci. 2015; 6: 4273
• 44 Wang X.-S, Yang G.-S, Zhao G. Tetrahedron: Asymmetry 2008; 19: 709
• 45 Ballini R, Palmieri A, Petrini M, Torregiani E. Org. Lett. 2006; 8: 4093
• 46 Yu L, Xie X, Wu S, Wang R, He W, Qin D, Liu Q, Jing L. Tetrahedron Lett. 2013; 54: 3675
• 47 Suzuki Y, Nemoto T, Kakugawa K, Hamajima A, Hamada Y. Org. Lett. 2012; 14: 2350
• 48 Xu Q.-L, Dai L.-X, You SL. Org. Lett. 2012; 14: 2579
• 49 Kanao K, Miyake Y, Nishibayashi Y. Organometallics 2010; 29: 2126
• 50 For a review on catalytic asymmetric dearomatizations of phenol and aniline derivatives, see: Wu W.-T, Zhang L, You S.-L. Chem. Soc. Rev. 2016; 45: 1570
• 51 Nemoto T, Ishige Y, Yoshida M, Kohno Y, Kanematsu M, Hamada Y. Org. Lett. 2010; 12: 5020
• 52 Yoshida M, Nemoto T, Zhao Z, Ishige Y, Hamada Y. Tetrahedron: Asymmetry 2012; 23: 859
• 53 Wu Q.-F, Liu W.-B, Zhuo C.-X, Rong Z.-Q, Ye K.-Y, You S.-L. Angew. Chem. Int. Ed. 2011; 50: 4455
• 54 Zhuo C.-X, You S.-L. Angew. Chem. Int. Ed. 2013; 52: 10056
• 55 Rousseaux S, García-Fortanet J, Del Aguila Sanchez MA, Buchwald SL. J. Am. Chem. Soc. 2011; 133: 9282
• 56 Xu R.-Q, Gu Q, Wu W.-T, Zhao Z.-A, You S.-L. J. Am. Chem. Soc. 2014; 136: 15469
• 57 Du K, Guo P, Chen Y, Cao Z, Wang Z, Tang W. Angew. Chem. Int. Ed. 2015; 54: 3033
• 58 Yang D, Wang L, Han F, Li D, Zhao D, Wang R. Angew. Chem. Int. Ed. 2015; 54: 2185
• 59 Yang D, Wang L, Kai M, Li D, Yao X, Wang R. Angew. Chem. Int. Ed. 2015; 54: 9523
• 60 Yang L, Zheng H, Luo L, Nan J, Liu J, Wang Y, Luan X. J. Am. Chem. Soc. 2015; 137: 4876
• 61 Wang S.-G, Liu X.-J, Zhao Q.-C, Zheng C, Wang S.-B, You S.-L. Angew. Chem. Int. Ed. 2015; 54: 14929