Synthesis 2016; 48(14): 2151-2164
DOI: 10.1055/s-0035-1561434
short review
© Georg Thieme Verlag Stuttgart · New York

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

Marc Montesinos-Magraner
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain   Email: [email protected]
,
Carlos Vila
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain   Email: [email protected]
,
Gonzalo Blay
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain   Email: [email protected]
,
José R. Pedro*
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 01 March 2016

Accepted: 07 March 2016

Publication Date:
20 April 2016 (online)


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

 
  • References

  • 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