Asymmetric binary acid catalysis: A regioselectivity switch between enantioselective 1,2- and 1,4-addition through different counteranions of InIII

Angewandte Chemie - International Edition

Volumn 50, Issue 29, 2011, Pages 6610-6614

  Lv, Jian ^a   Zhang, Long ^a   Zhou, Yueming ^b   Nie, Zongxiu ^b   Luo, Sanzhong ^a   Cheng, Jin Pei ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

asymmetric catalysis; counterion effect; Friedel Crafts alkylation; organocatalysis; switchable regioselectivity

Indexed keywords

ASYMMETRIC CATALYSIS; COUNTER-ION EFFECTS; FRIEDEL-CRAFTS ALKYLATION; ORGANOCATALYSIS; SWITCHABLE;

ADDITION REACTIONS; CATALYSIS; ENANTIOSELECTIVITY; INDIUM; NEGATIVE IONS; REACTION KINETICS;

REGIOSELECTIVITY;

INDIUM; INDOLE DERIVATIVE; PHOSPHORIC ACID;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; INDIUM; INDOLES; PHOSPHORIC ACIDS; STEREOISOMERISM;

EID: 79959935295     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101254     Document Type: Article

References (55)

1. For reviews on asymmetric Friedel-Crafts reactions, see
2. S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190-2201
3. T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903-2915
4. M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566
5. Angew. Chem. Int. Ed. 2004, 43, 550-556
6. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786-9824
7. Angew. Chem. Int. Ed. 2009, 48, 9608-9644
8. V. Terrasson, R. M. de Figueiredo, J. M. Campagne, Eur. J. Org. Chem. 2010, 2635-2655.
9. For leading examples on metal-catalyzed asymmetric Friedel-Crafts reactions, see: copper catalyzed
10. K. B. Jensen, J. Thorhauge, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2001, 113, 164-167
11. Angew. Chem. Int. Ed. 2001, 40, 160-163
12. J. Zhou, Y. Tang, J. Am. Chem. Soc. 2002, 124, 9030-9033
13. K. A. Jørgensen, Synthesis 2003, 1117-1125
14. M. Bandini, M. Fagioli, M. Garavelli, A. Melloni, V. Trigari, A. Umani-Ronchi, J. Org. Chem. 2004, 69, 7511-7518
15. C. Palomo, M. Oiarbide, B. G. Kardak, J. M. Garcia, A. Linden, J. Am. Chem. Soc. 2005, 127, 4154-4155
16. Y. X. Jia, S. F. Zhu, Y. Yang, Q. L. Zhou, J. Org. Chem. 2006, 71, 75-80
17. S. Yamazaki, Y. Iwata, J. Org. Chem. 2006, 71, 739-743
18. R. Rasappan, M. Hager, A. Gissibl, O. Reiser, Org. Lett. 2006, 8, 6099-6102; scandium catalyzed
19. D. A. Evans, K. A. Scheidt, K. R. Fandrick, H. W. Lam, J. Wu, J. Am. Chem. Soc. 2003, 125, 10780-10781
20. D. A. Evans, K. R. Fandrick, H.-J. Song, J. Am. Chem. Soc. 2005, 127, 8942-8943
21. D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc. 2007, 129, 10029-10041
22. Y. Liu, D. Shang, X. Zhou, Y. Zhu, L. Lin, X. Liu, X. Feng, Org. Lett. 2010, 12, 180-183; iron catalyzed
23. L. Yang, Q. Zhu, S. Guo, B. Qian, C. Xia, H. Huang, Chem. Eur. J. 2010, 16, 1638-1645.
24. For leading examples on immnium-based catalysis of asymmetric Friedel-Crafts alkylations, see
25. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370-4371
26. J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172-1173
27. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894-7895
28. N. Halland, T. Hansen, K. A. Jørgensen, Angew. Chem. 2003, 115, 5105-5107
29. Angew. Chem. Int. Ed. 2003, 42, 4955-4957
30. G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403-1405
31. L. Hong, L. Wang, C. Chen, B. Zhang, R. Wang, Adv. Synth. Catal. 2009, 351, 772-778.
32. For a leading example of asymmetric Friedel-Crafts alkylation catalyzed by chiral phosphoric acid, see:, M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603-606
33. Angew. Chem. Int. Ed. 2008, 47, 593-596.
34. For examples of asymmetric 1,2-addition of α,β-unsaturated carbonyl compounds: aldol reaction
35. C. Zheng, Y. Wu, X. Wang, G. Zhao, Adv. Synth. Catal. 2008, 350, 2690-2694
36. P. Li, J. Zhao, F. Li, A. S. C. Chan, F. Y. Kwong, Org. Lett. 2010, 12, 5616-5619; Henry reaction
37. C. Christensen, K. Juhl, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67, 4875-4881; rhodium-catalyzed addition of arylboronic acids to α-keto esters
38. H.-F. Duan, J.-H. Xie, X.-C. Qiao, L.-X. Wang, Q.-L. Zhou, Angew. Chem. 2008, 120, 4423-4425
39. Angew. Chem. Int. Ed. 2008, 47, 4351-4353.
40. H. Li, Y.-Q. Wang, L. Deng, Org. Lett. 2006, 8, 4063-4065.
41. For pioneer contributions on chiral phosphoric acid catalysis, see
42. M. Terada, Chem. Commun. 2008, 4097-4112
43. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758.
44. J. Lv, X. Li, L. Zhang, S. Luo, J.-P. Cheng, Org. Lett. 2010, 12, 1096-1099.
45. For a review on combined phosphoric acid and metal catalysis, see:, M. Rueping, R. M. Koenigs, I. Atodiresei, Chem. Eur. J. 2010, 16, 9350-9365.
46. The exploration of aliphatic β,γ-unsaturated α-keto esters has been limited by the difficulities encountered in synthesizing these substrates. For a recent example, see:, D. Belmessieri, L. C. Morrill, C. Simal, A. M. Z. Slawin, A. D. Smith, J. Am. Chem. Soc. 2011, 133, 2714-2720; for the only available synthetic method, see
47. H. Sugimura, Y. Kazuhiro, Bull. Chem. Soc. Jpn. 1992, 65, 3209-3211.
48. CCDC 810832 (5c) and 813841 (4i) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
49. 3 with 1a or 1e in 1:1 or 1:2 ratio, see the Supporting Information for details.
50. Acid Catalysis in Modern Organic Sythesis (Ed.:, H. Yamamoto, K. Ishihara,), Wiley-VCH, Weinheim, 2008
51. H. Yamamoto, K. Futatsugi, Angew. Chem. 2005, 117, 1958-1977
52. Angew. Chem. Int. Ed. 2005, 44, 1924-1942.
53. B. L. Pagenkopf, E. M. Carreira, Chem. Eur. J. 1999, 5, 3437-3442.
54. 3 (see the Supporting Information for the IR spectra).
55. S. E. Denmark, G. L. Beutner, T. Wynn, M. D. Eastgate, J. Am. Chem. Soc. 2005, 127, 3774-3789.