Enantioselective activation of stable carboxylate esters as enolate equivalents via N-heterocyclic carbene catalysts

Organic Letters

Volumn 14, Issue 8, 2012, Pages 2154-2157

  Hao, Lin ^a   Du, Yu ^a   Lv, Hui ^a   Chen, Xingkuan ^a   Jiang, Huishen ^a   Shao, Yaling ^a   Chi, Yonggui Robin ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CARBOXYLIC ACID; DRUG DERIVATIVE; ESTER; HETEROCYCLIC COMPOUND; IMINE; METHANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CARBOXYLIC ACIDS; CATALYSIS; ESTERS; HETEROCYCLIC COMPOUNDS; IMINES; METHANE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84860162011     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300676w     Document Type: Article

References (81)

1. Fu, G. C. Acc. Chem. Res. 2000, 33, 412-420
2. Fu, G. C. Acc. Chem. Res. 2004, 37, 542-547
3. Wurz, R. P. Chem. Rev. 2007, 107, 5570-5595
4. France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985-3012
5. France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592-600
6. Gaunt, M. J.; Johansson, C. C. C. Chem. Rev. 2007, 107, 5596-5605
7. Paull, D. H.; Weatherwax, A.; Lectka, T. Tetrahedron 2009, 65, 6771-6803
8. Duguet, N.; Campbell, C. D.; Slawin, A. M. Z.; Smith, A. D. Org. Biomol. Chem. 2008, 6, 1108-1113
9. Concellon, C.; Duguet, N.; Smith, A. D. Adv. Synth. Catal. 2009, 351, 3001-3009
10. Douglas, J.; Ling, K. B.; Concellon, C.; Churchill, G.; Slawin, A. M. Z.; Smith, A. D. Eur. J. Org. Chem. 2010, 5863-5869
11. He, L.; Lv, H.; Zhang, Y.; Ye, S. J. Org. Chem. 2008, 73, 8101-8103
12. Zhang, Y. R.; He, L.; Wu, X.; Shao, P. L.; Ye, S. Org. Lett. 2008, 10, 277-280
13. Huang, X. L.; He, L.; Shao, P. L.; Ye, S. Angew. Chem., Int. Ed. 2009, 48, 192-195
14. Jian, T. Y.; He, L.; Tang, C.; Ye, S. Angew. Chem., Int. Ed. 2011, 50, 9104-9107
15. Jian, T. Y.; Shao, P. L.; Ye, S. Chem. Commun. 2011, 47, 2381-2383
16. Belmessieri, D.; Morrill, L. C.; Simal, C.; Slawin, A. M. Z.; Smith, A. D. J. Am. Chem. Soc. 2011, 133, 2714-2720
17. Morrill, L. C.; Lebl, T.; Slawin, A. M. Z.; Smith, A. D. Chem. Sci. 2012, DOI: 10.1039/C2SC20171B
18. For a selected review of enolate generations using phase-transfer catalysts, see: Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013-3028
19. For a recent review on the related "chiral enol equivalents" (enamine catalysis), see: Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569
20. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541
21. Zeitler, K. Angew. Chem., Int. Ed. 2005, 44, 7506-7510
22. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606-5655
23. Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988-3000
24. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691-2698
25. Rovis, T. Chem. Lett. 2008, 37, 2-7
26. Arduengo, A. J., III; Iconaru, L. I. Dalton Trans. 2009, 6903-6914
27. Phillips, E. M.; Chan, A.; Scheidt, K. A. Aldrichimica Acta 2009, 42, 55-66
28. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2011, 291, 77-144
29. Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182-1195
30. Hirano, K.; Piel, I.; Glorius, F. Chem. Lett. 2011, 40, 786-791
31. Chiang, P.-C.; Bode, J. W. TCI MAIL 2011, 149, 2-17
32. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336-5346
33. Rong, Z. Q.; Zhang, W.; Yang, G. Q.; You, S. L. Curr. Org. Chem. 2011, 15, 3077-3090
34. Vora, H. U.; Rovis, T. Aldrichimica Acta 2011, 44, 3-11
35. Glorius, F.; Hirano, K. Ernst Schering Foundation Symposium Proceedings 2008, 2, 159-181
36. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314-325
37. Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53-57
38. Chow, K. Y. K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126-8127
39. Reynolds, N. T.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518-9519
40. Kawanaka, Y.; Phillips, E. M.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 18028-18029
41. Reynolds, N. T.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 16406-16407
42. He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088-15089
43. Alcaide, B.; Almendros, P.; Cabrero, G.; Ruiz, M. P. Chem. Commun. 2007, 4788-4790
44. Bode, J. W.; Sohn, S. S. J. Am. Chem. Soc. 2007, 129, 13798-13799
45. Li, G. Q.; Li, Y.; Dai, L. X.; You, S. L. Org. Lett. 2007, 9, 3519-3521
46. Vora, H. U.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 13796-13797
47. Du, D.; Li, L. X.; Wang, Z. W. J. Org. Chem. 2009, 74, 4379-4382
48. Kobayashi, S.; Kinoshita, T.; Uehara, H.; Sudo, T.; Ryu, I. Org. Lett. 2009, 11, 3934-3937
49. Li, G. Q.; Dai, L. X.; You, S. L. Org. Lett. 2009, 11, 1623-1625
50. Phillips, E. M.; Wadamoto, M.; Roth, H. S.; Ott, A. W.; Scheidt, K. A. Org. Lett. 2009, 11, 105-108
51. Wang, L.; Thai, K.; Gravel, M. Org. Lett. 2009, 11, 891-893
52. Vora, H. U.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 2860-2861
53. Ling, K. B.; Smith, A. D. Chem. Commun. 2011, 47, 373-375
54. He, M.; Beahm, B. J.; Bode, J. W. Org. Lett. 2008, 10, 3817-3820 and ref 7
55. He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418-8420
56. Burstein, C.; Tschan, S.; Xie, X. L.; Glorius, F. Synthesis 2006, 2418-2439
57. Phillips, E. M.; Wadamoto, M.; Chan, A.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 3107-3110
58. Wadamoto, M.; Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 10098-10099
59. Kaeobamrung, J.; Kozlowski, M. C.; Bode, J. W. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20661-20665
60. Fang, X.; Chen, X.; Chi, Y. R. Org. Lett. 2011, 13, 4708-4711
61. Schrader, W. W.; Handayani, P. P.; Burstein, C.; Glorius, F. Chem. Commun. 2007, 716-718
62. Mahatthananchai, J.; Bode, J. W. Chem. Sci. 2012, 3, 192-197
63. Zhao, Y. M.; Tam, Y.; Wang, Y. J.; Li, Z.; Sun, J. Org. Lett. 2012, 14, 1398-1401
64. Liu, G.; Wilkerson, P. D.; Toth, C. A.; Xu, H. Org. Lett. 2012, 14, 858-861
65. Grasa, G. A.; Singh, R.; Nolan, S. P. Synthesis 2004, 971-985
66. Thomson, J. E.; Rix, K.; Smith, A. D. Org. Lett. 2006, 8, 3785-3788
67. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176-14177
68. Candish, L.; Lupton, D. W. Org. Lett. 2010, 12, 4836-4839
69. Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583-3586
70. Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587-3590
71. Sarkar, S. D.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190-1191
72. Radt, C. W.; Ried, W. Angew. Chem., Int. Ed. 1963, 2, 397
73. Bekele, T.; Shah, M. H.; Wolfer, J.; Abraham, C. J.; Weatherwax, A.; Lectka, T. J. Am. Chem. Soc. 2006, 128, 1810-1811
74. Paull, D. H.; Wolfer, J.; Grebinski, J. W.; Weatherwax, A.; Lectka, T. Chimia 2007, 61, 240-246
75. Abraham, C. J.; Paill, D. H.; Bekele, T.; Scerba, M. T.; Lectka, T.; Dudding, T. J. Am. Chem. Soc. 2008, 130, 17085-17094
76. Struble, J. R.; Kaeobamrung, J.; Bode, J. W. Org. Lett. 2008, 10, 957-960
77. Fang, X. Q.; Chen, X. K.; Chi, Y. R. Org. Lett. 2011, 13, 4708-4711
78. Lv, H.; Mo, J. M.; Fang, X. Q.; Chi, Y. R. Org. Lett. 2011, 13, 5366-5369
79. Han, B.; Li, J. L.; Ma, C.; Zhang, S. J.; Chen, Y. C. Angew. Chem., Int. Ed. 2008, 47, 9971-9974
80. Han, B.; He, Z. Q.; Li, J. L.; Li, R.; Jiang, K.; Liu, T. Y.; Chen, Y. C. Angew. Chem., Int. Ed. 2009, 48, 5474-5477
81. After submission of this manuscript, Smiths group reported a chiral isothiourea-catalyzed transformation of carboxylic acids to similar products. Simal, C.; Lebl, T.; Slawin, A. M. Z.; Smith, A. D. Angew. Chem., Int. Ed. 2012, 10.1002/anie.201109061