Synthesis 2015; 47(23): 3629-3644
DOI: 10.1055/s-0035-1560356
review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Catalytic Asymmetric Reactions of o-Quinone Methides

Zhaobin Wang
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, P. R. of China   Email: sunjw@ust.hk
,
Jianwei Sun*
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, P. R. of China   Email: sunjw@ust.hk
› Author Affiliations
Further Information

Publication History

Received: 30 August 2015

Accepted after revision: 14 September 2015

Publication Date:
21 October 2015 (online)


Abstract

This review summarizes recent advances in catalytic asymmetric reactions of o-quinone methides, an important family of species for organic synthesis. In the past decade, various catalytic systems have been developed for these reactions. This review is organized by the type of catalyst employed.

1 Introduction

2 Transition-Metal Catalysis

3 Phase-Transfer Catalysis

4 N-Heterocyclic Carbene Catalysis

5 Chiral Brønsted Acid Catalysis

6 Chiral Diol Catalysis

7 Bifunctional Chiral Brønsted Base Catalysis

8 Conclusion and Outlook

 
  • References


    • For selected reviews about o-QMs, see:
    • 1a Amouri H, Le Bras J. Acc. Chem. Res. 2002; 35: 501
    • 1b Van De Water RW, Pettus TR. R. Tetrahedron 2002; 58: 5367
    • 1c Quinone Methides . Rokita SE. Wiley; Hoboken: 2009
    • 1d Pathak TP, Sigman MS. J. Org. Chem. 2011; 76: 9210
    • 1e Willis NJ, Bray CD. Chem. Eur. J. 2012; 18: 9160
    • 1f Bai WJ, David JG, Feng ZG, Weaver MG, Wu KL, Pettus TR. Acc. Chem. Res. 2014; 47: 3655
    • 1g Caruana L, Fochi M, Bernardi L. Molecules 2015; 20: 11733
    • 2a Fries K, Kann KI. Liebigs Ann. Chem. 1907; 353: 335
    • 2b Chapman OL, McIntosh CL. J. Chem. Soc. D 1971; 383
    • 3a Gardner PD, Rafsanjani HS, Rand L. J. Am. Chem. Soc. 1959; 81: 3364
    • 3b Gardner PD, Sarrafizadeh R H, Brandon RL. J. Am. Chem. Soc. 1959; 81: 5515
    • 3c Cavitt SB, Sarrafizadeh R H, Gardner PD. J. Org. Chem. 1962; 27: 1211
    • 3d Merijan A, Shoulders BA, Gardner PD. J. Org. Chem. 1963; 28: 2148
    • 3e Merijan A, Gardner PD. J. Org. Chem. 1965; 30: 3965
    • 4a Amouri H, Besace Y, Bras JL, Vaissermann J. J. Am. Chem. Soc. 1998; 120: 6171
    • 4b Amouri H, Vaissermann J, Rager MN, Grotjahn DB. Organometallics 2000; 19: 1740
    • 4c Amouri H, Vaissermann J, Rager MN, Grotjahn DB. Organometallics 2000; 19: 5143

      For selected reviews about asymmetric catalysis, see:
    • 5a Noyori R. Angew. Chem. Int. Ed. 2002; 41: 2008
    • 5b Hawkins JM, Watson TJ. N. Angew. Chem. Int. Ed. 2004; 43: 3224
    • 5c Taylor MS, Jacobsen EN. Angew. Chem. Int. Ed. 2006; 45: 1520
    • 5d Arena CG, Arico G. Curr. Org. Chem. 2010; 14: 546
    • 5e Desimoni G, Faita G, Joergensen KA. Chem. Rev. 2011; 111: PR284
    • 5f Carroll MP, Guiry PJ. Chem. Soc. Rev. 2014; 43: 819
    • 5g Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
  • 6 Selenski C, Pettus TR. R. J. Org. Chem. 2004; 69: 9196
  • 7 Zhang Y, Sigman MS. J. Am. Chem. Soc. 2007; 129: 3076
  • 8 Jensen KH, Pathak TP, Zhang Y, Sigman MS. J. Am. Chem. Soc. 2009; 131: 17074
  • 9 Jensen KH, Webb JD, Sigman MS. J. Am. Chem. Soc. 2010; 132: 17471
  • 10 Pathak TP, Gligorich KM, Welm BE, Sigman MS. J. Am. Chem. Soc. 2010; 132: 7870
  • 11 Jana R, Pathak TP, Jensen KH, Sigman MS. Org. Lett. 2012; 14: 4074
  • 12 Hu H, Liu Y, Guo J, Lin L, Xu Y, Liu X, Feng X. Chem. Commun. 2015; 51: 3835
  • 13 Huang Y, Hayashi T. J. Am. Chem. Soc. 2015; 137: 7556
  • 14 Alden-Danforth E, Scerba MT, Lectka T. Org. Lett. 2008; 10: 4951
  • 15 Lv H, You L, Ye S. Adv. Synth. Catal. 2009; 351: 2822
  • 16 Lv H, Jia W.-Q, Sun L.-H, Ye S. Angew. Chem. Int. Ed. 2013; 52: 8607
  • 17 Izquierdo J, Orue A, Scheidt KA. J. Am. Chem. Soc. 2013; 135: 10634
  • 18 Lee A, Scheidt KA. Chem. Commun. 2015; 51: 3407
  • 19 Wilcke D, Herdtweck E, Bach T. Synlett 2011; 1235
  • 20 Rueping M, Uria U, Lin M.-Y, Atodiresei I. J. Am. Chem. Soc. 2011; 133: 3732
  • 21 El-Sepelgy O, Haseloff S, Alamsetti SK, Schneider C. Angew. Chem. Int. Ed. 2014; 53: 7923
  • 22 Hsiao C.-C, Liao H.-H, Rueping M. Angew. Chem. Int. Ed. 2014; 53: 13258
  • 23 Saha S, Alamsetti SK, Schneider C. Chem. Commun. 2015; 51: 1461
  • 24 Zhao W, Wang Z, Chu B, Sun J. Angew. Chem. Int. Ed. 2015; 54: 1910
  • 25 Wang Z, Ai F, Wang Z, Zhao W, Zhu G, Lin Z, Sun J. J. Am. Chem. Soc. 2015; 137: 383
  • 26 Li M.-L, Chen D.-F, Luo S.-W, Wu X. Tetrahedron: Asymmetry 2015; 26: 219
  • 27 Dai W, Lu H, Jiang X.-L, Gao T.-T, Shi F. Tetrahedron: Asymmetry 2015; 26: 109
  • 28 Saha S, Schneider C. Chem. Eur. J. 2015; 21: 2348
  • 29 Saha S, Schneider C. Org. Lett. 2015; 17: 648
  • 30 Zhao J.-J, Sun S.-B, He S.-H, Wu Q, Shi F. Angew. Chem. Int. Ed. 2015; 54: 5460
  • 31 Hsiao C.-C, Raja S, Liao H.-H, Atodiresei I, Rueping M. Angew. Chem. Int. Ed. 2015; 54: 5762
  • 32 Tsui GC, Liu L, List B. Angew. Chem. Int. Ed. 2015; 54: 7703
  • 33 Luan Y, Schaus SE. J. Am. Chem. Soc. 2012; 134: 19965
  • 34 Grayson MN, Goodman JM. J. Org. Chem. 2015; 80: 2056
  • 35 Chen M.-W, Cao L.-L, Ye Z.-S, Jiang G.-F, Zhou Y.-G. Chem. Commun. 2013; 49: 1660
  • 36 Guo W, Wu B, Zhou X, Chen P, Wang X, Zhou Y.-G, Liu Y, Li C. Angew. Chem. Int. Ed. 2015; 54: 4522
  • 37 Caruana L, Mondatori M, Corti V, Morales S, Mazzanti A, Fochi M, Bernardi L. Chem. Eur. J. 2015; 21: 6037
  • 38 Adili A, Tao Z.-L, Chen D.-F, Han Z.-Y. Org. Biomol. Chem. 2015; 13: 2247
  • 39 Wu B, Gao X, Yan Z, Huang W.-X, Zhou Y.-G. Tetrahedron Lett. 2015; 56: 4334

    • For asymmetric examples about aza-o-QMs, see:
    • 40a Yang Q.-Q, Wang Q, An J, Chen J.-R, Lu L.-Q, Xiao W.-J. Chem. Eur. J. 2013; 19: 8401
    • 40b Lee A, Younai A, Price CK, Izquierdo J, Mishra RK, Scheidt KA. J. Am. Chem. Soc. 2014; 136: 10589
  • 41 Parra A, Tortosa M. ChemCatChem 2015; 7: 1524