Recent Advances in Catalytic Asymmetric Reactions of o -Quinone Methides

Synthesis (Germany)

Volumn 47, Issue 23, 2015, Pages 3629-3644

  Wang, Zhaobin ^a   Sun, Jianwei ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

asymmetric addition; asymmetric catalysis; cycloaddition; o quinone methides; organocatalysis

Indexed keywords

CYCLOADDITION; ORGANIC COMPOUNDS; POLYOLS; TRANSITION METALS;

ASYMMETRIC ADDITION; ASYMMETRIC CATALYSIS; CATALYTIC ASYMMETRIC REACTIONS; N-HETEROCYCLIC CARBENES; O-QUINONE METHIDES; ORGANOCATALYSIS; PHASE TRANSFER CATALYSIS; TRANSITION METAL CATALYSIS;

CATALYSIS;

2 QUINONE METHIDE DERIVATIVE; BRONSTED ACID; CARBENOID; N HETEROCYCLIC CARBENE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

BIFUNCTIONAL CHIRAL BRONSTED BASE CATALYSIS; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRAL BRONSTED ACID CATALYSIS; CHIRAL DIOL CATALYSIS; CONCENTRATION (PARAMETERS); ENANTIOSELECTIVITY; PHASE TRANSFER CATALYSIS; REVIEW; TRANSITION METAL CATALYSIS;

EID: 84947750546     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0035-1560356     Document Type: Review

References (61)

1. Amouri H., Le Bras J. Acc. Chem. Res.: 2002; 35 501
2. Van De Water R. W., Pettus T. R. R. Tetrahedron: 2002; 58 5367
3. Quinone Methides. Rokita S. E. Wiley Hoboken: 2009
4. Pathak T. P., Sigman M. S. J. Org. Chem.: 2011; 76 9210
5. Willis N. J., Bray C. D. Chem. Eur. J.: 2012; 18 9160
6. Bai W. J., David J. G., Feng Z. G., Weaver M. G., Wu K. L., Pettus T. R. Acc. Chem. Res.: 2014; 47 3655
7. Caruana L., Fochi M., Bernardi L. Molecules: 2015; 20 11733
8. Fries K., Kann K. I. Liebigs Ann. Chem.: 1907; 353 335
9. Chapman O. L., McIntosh C. L. J. Chem. Soc. D: 1971; 383
10. Gardner P. D., Rafsanjani H. S., Rand L. J. Am. Chem. Soc.: 1959; 81 3364
11. Gardner P. D., Sarrafizadeh R H., Brandon R. L. J. Am. Chem. Soc.: 1959; 81 5515
12. Cavitt S. B., Sarrafizadeh R H., Gardner P. D. J. Org. Chem.: 1962; 27 1211
13. Merijan A., Shoulders B. A., Gardner P. D. J. Org. Chem.: 1963; 28 2148
14. Merijan A., Gardner P. D. J. Org. Chem.: 1965; 30 3965
15. Amouri H., Besace Y., Bras J. L., Vaissermann J. J. Am. Chem. Soc.: 1998; 120 6171
16. Amouri H., Vaissermann J., Rager M. N., Grotjahn D. B. Organometallics: 2000; 19 1740
17. Amouri H., Vaissermann J., Rager M. N., Grotjahn D. B. Organometallics: 2000; 19 5143
18. Noyori R. Angew. Chem. Int. Ed.: 2002; 41 2008
19. Hawkins J. M., Watson T. J. N. Angew. Chem. Int. Ed.: 2004; 43 3224
20. Taylor M. S., Jacobsen E. N. Angew. Chem. Int. Ed.: 2006; 45 1520
21. Arena C. G., Arico G. Curr. Org. Chem.: 2010; 14 546
22. Desimoni G., Faita G., Joergensen K. A. Chem. Rev.: 2011; 111 PR284
23. Carroll M. P., Guiry P. J. Chem. Soc. Rev.: 2014; 43 819
24. Parmar D., Sugiono E., Raja S., Rueping M. Chem. Rev.: 2014; 114 9047
25. Selenski C., Pettus T. R. R. J. Org. Chem.: 2004; 69 9196
26. Zhang Y., Sigman M. S. J. Am. Chem. Soc.: 2007; 129 3076
27. Jensen K. H., Pathak T. P., Zhang Y., Sigman M. S. J. Am. Chem. Soc.: 2009; 131 17074
28. Jensen K. H., Webb J. D., Sigman M. S. J. Am. Chem. Soc.: 2010; 132 17471
29. Pathak T. P., Gligorich K. M., Welm B. E., Sigman M. S. J. Am. Chem. Soc.: 2010; 132 7870
30. Jana R., Pathak T. P., Jensen K. H., Sigman M. S. Org. Lett.: 2012; 14 4074
31. Hu H., Liu Y., Guo J., Lin L., Xu Y., Liu X., Feng X. Chem. Commun.: 2015; 51 3835
32. Huang Y., Hayashi T. J. Am. Chem. Soc.: 2015; 137 7556
33. Alden-Danforth E., Scerba M. T., Lectka T. Org. Lett.: 2008; 10 4951
34. Lv H., You L., Ye S. Adv. Synth. Catal.: 2009; 351 2822
35. Lv H., Jia W.-Q, Sun L.-H, Ye S. Angew. Chem. Int. Ed.: 2013; 52 8607
36. Izquierdo J., Orue A., Scheidt K. A. J. Am. Chem. Soc.: 2013; 135 10634
37. Lee A., Scheidt K. A. Chem. Commun.: 2015; 51 3407
38. Wilcke D., Herdtweck E., Bach T. Synlett: 2011; 1235
39. Rueping M., Uria U., Lin M.-Y, Atodiresei I. J. Am. Chem. Soc.: 2011; 133 3732
40. El-Sepelgy O., Haseloff S., Alamsetti S. K., Schneider C. Angew. Chem. Int. Ed.: 2014; 53 7923
41. Hsiao C.-C, Liao H.-H, Rueping M. Angew. Chem. Int. Ed.: 2014; 53 13258
42. Saha S., Alamsetti S. K., Schneider C. Chem. Commun.: 2015; 51 1461
43. Zhao W., Wang Z., Chu B., Sun J. Angew. Chem. Int. Ed.: 2015; 54 1910
44. Wang Z., Ai F., Wang Z., Zhao W., Zhu G., Lin Z., Sun J. J. Am. Chem. Soc.: 2015; 137 383
45. Li M.-L, Chen D.-F, Luo S.-W, Wu X. Tetrahedron: Asymmetry: 2015; 26 219
46. Dai W., Lu H., Jiang X.-L, Gao T.-T, Shi F. Tetrahedron: Asymmetry: 2015; 26 109
47. Saha S., Schneider C. Chem. Eur. J.: 2015; 21 2348
48. Saha S., Schneider C. Org. Lett.: 2015; 17 648
49. Zhao J.-J, Sun S.-B, He S.-H, Wu Q., Shi F. Angew. Chem. Int. Ed.: 2015; 54 5460
50. Hsiao C.-C, Raja S., Liao H.-H, Atodiresei I., Rueping M. Angew. Chem. Int. Ed.: 2015; 54 5762
51. Tsui G. C., Liu L., List B. Angew. Chem. Int. Ed.: 2015; 54 7703
52. Luan Y., Schaus S. E. J. Am. Chem. Soc.: 2012; 134 19965
53. Grayson M. N., Goodman J. M. J. Org. Chem.: 2015; 80 2056
54. Chen M.-W, Cao L.-L, Ye Z.-S, Jiang G.-F, Zhou Y.-G. Chem. Commun.: 2013; 49 1660
55. Guo W., Wu B., Zhou X., Chen P., Wang X., Zhou Y.-G, Liu Y., Li C. Angew. Chem. Int. Ed.: 2015; 54 4522
56. Caruana L., Mondatori M., Corti V., Morales S., Mazzanti A., Fochi M., Bernardi L. Chem. Eur. J.: 2015; 21 6037
57. Adili A., Tao Z.-L, Chen D.-F, Han Z.-Y. Org. Biomol. Chem.: 2015; 13 2247
58. Wu B., Gao X., Yan Z., Huang W.-X, Zhou Y.-G. Tetrahedron Lett.: 2015; 56 4334
59. Yang Q.-Q, Wang Q., An J., Chen J.-R, Lu L.-Q, Xiao W.-J. Chem. Eur. J.: 2013; 19 8401
60. Lee A., Younai A., Price C. K., Izquierdo J., Mishra R. K., Scheidt K. A. J. Am. Chem. Soc.: 2014; 136 10589
61. Parra A., Tortosa M. ChemCatChem: 2015; 7 1524