Rh(I)-catalyzed asymmetric 1,2-additions of arylboronic acids to isatins with chiral sulfur-alkene hybrid ligands

Tetrahedron Letters

Volumn 55, Issue 33, 2014, Pages 4581-4584

  Feng, Xiangqing ^a   Nie, Yanzhao ^b   Zhang, Lanqiong ^b   Yang, Jing ^b   Du, Haifeng ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

1,2 Addition; 3 Aryl 3 hydroxy 2 oxindoles; Asymmetric catalysis; Chiral sulfur alkene ligands; Rhodium catalyzed

Indexed keywords

ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; ISATIN DERIVATIVE; LIGAND; RHODIUM; SULFUR DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; SYNTHESIS;

EID: 84908155287     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.06.074     Document Type: Article

References (53)

1. H.R. Howard, J.A. Lowe III, T.F. Seeger, P.A. Seymour, S.H. Zorn, P.R. Maloney, F.E. Ewing, M.E. Newman, A.W. Schmidt, J.S. Furman, G.L. Robinson, E. Jackson, C. Johnson, and J. Morrone J. Med. Chem. 39 1996 143 148
2. S. Hibino, and T. Choshi Nat. Prod. Rep. 19 2002 148 180
3. Y.-Q. Tang, I. Sattler, R. Thiericke, S. Grabley, and X.-Z. Feng Eur. J. Org. Chem. 2001 261 267
4. M. Somei, and S. Yamada Nat. Prod. Rep. 20 2003 216 242
5. K.C. Nicolaou, J. Hao, M.V. Reddy, P.B. Rao, G. Rassias, S.A. Synder, X. Huang, D.Y.-K. Chen, W.E. Brenzovich, N. Giuseppone, P. Giannakakou, and A. O'Brate J. Am. Chem. Soc. 126 2004 12897 12906
6. T. Tokunaga, W.E. Hume, T. Umezome, K. Okazaki, Y. Ueki, K. Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji, H. Noguchi, and R. Nagata J. Med. Chem. 44 2001 4641 4649
7. T. Tokunaga, W.E. Hume, J. Nagamine, T. Kawamura, M. Taiji, and R. Nagata Bioorg. Med. Chem. Lett. 15 2005 1789 1792
8. K. Bernard, S. Bogliolo, and J. Ehrenfeld Br. J. Pharmacol. 144 2005 1037 1050
9. Di Malta, A.; Garcia, G.; Roux, R.; Schoentjes, B.; Serradeil-le Gal, C.; Tonnerre, B. J. Wagnon, PCT Int. Appl. No.WO2003008407, 2003.
10. S. Barroso, G. Blay, L. Cardona, I. Fernández, B. García, and J.R. Pedro J. Org. Chem. 69 2004 6821 6829
11. P. Hewawasam, M. Erway, S.L. Moon, J. Knipe, H. Weiner, C.G. Boissard, D.J. Post-Munson, Q. Gao, S. Huang, V.K. Gribkoff, and N.A. Meanwell J. Med. Chem. 45 2002 1487 1489
12. K. Funabashi, M. Jachmann, M. Kanai, and M. Shibasaki Angew. Chem., Int. Ed. 42 2003 5489 5492
13. Y.-X. Jia, J.M. Hillgren, E.L. Watson, S.P. Marsden, and E.P. Kündig Chem. Commun. 2008 4040 4042
14. N.V. Hanhan, A.H. Sahin, T.W. Chang, J.C. Fettinger, and A.K. Franz Angew. Chem., Int. Ed. 49 2010 744 747
15. R. Shintani, M. Inoue, and T. Hayashi Angew. Chem., Int. Ed. 45 2006 3353 3356
16. P.Y. Toullec, R.B.C. Jagt, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Org. Lett. 8 2006 2715 2718
17. D. Tomita, K. Yamatsugu, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 131 2009 6946 6948
18. H. Lai, Z. Huang, Q. Wu, and Y. Qin J. Org. Chem. 74 2009 283 288
19. J. Gui, G. Chen, P. Cao, and J. Liao Tetrahedron: Asymmetry 23 2012 554 563
20. Y. Yamamoto, M. Yohda, T. Shirai, H. Ito, and N. Miyaura Chem. Asian J. 7 2012 2446 2449
21. Q. Li, P. Wan, S. Wang, Y. Zhuang, L. Li, Y. Zhou, Y. He, R. Cao, L. Qiu, and Z. Zhou Appl. Catal. A: Gen. 458 2013 201 206
22. R. Shintani, K. Takatsu, and T. Hayashi Chem. Commun. 46 2010 6822 6824
23. Z. Liu, P. Gu, M. Shi, P. McDowell, and G. Li Org. Lett. 13 2011 2314 2317
24. For leading reviews on chiral olefin ligands in asymmetric catalysis, see: F. Glorius Angew. Chem., Int. Ed. 43 2004 3364 3366
25. J.B. Johnson, and T. Rovis Angew. Chem., Int. Ed. 47 2008 840 871
26. C. Defieber, H. Grützmacher, and E.M. Carreira Angew. Chem., Int. Ed. 47 2008 4482 4502
27. R. Shintani, and T. Hayashi Aldrichim. Acta 42 2009 31 38
28. C.-G. Feng, M.-H. Xu, and G.-Q. Lin Synlett 2011 1345 1356
29. P. Tian, H.-Q. Dong, and G.-Q. Lin ACS Catal. 2 2012 95 119
30. X. Feng, and H. Du Asian J. Org. Chem. 1 2012 204 213
31. Y. Li, and M.-H. Xu Chem. Commun. 50 2014 3771 3782
32. For selected examples of chiral olefin ligands, see: T. Hayashi, K. Ueyama, N. Tokunaga, and K. Yoshida J. Am. Chem. Soc. 125 2003 11508 11509
33. C. Fischer, C. Defieber, T. Suzuki, and E.M. Carreira J. Am. Chem. Soc. 126 2004 1628 1629
34. Z.-Q. Wang, C.-G. Feng, M.-H. Xu, and G.-Q. Lin J. Am. Chem. Soc. 129 2007 5336 5337
35. Q. Li, Z. Dong, and Z.-X. Yu Org. Lett. 13 2011 1122 1125
36. B.M. Trost, A.C. Burns, and T. Tautz Org. Lett. 13 2011 4566 4569
37. X. Hu, M. Zhuang, Z. Cao, and H. Du Org. Lett. 11 2009 4744 4747
38. X. Hu, Z. Cao, Z. Liu, Y. Wang, and H. Du Adv. Synth. Catal. 352 2010 651 655
39. Y. Wang, X. Hu, and H. Du Org. Lett. 12 2010 5482 5485
40. Z. Cao, and H. Du Org. Lett. 12 2010 2602 2605
41. T. Thaler, L.-N. Guo, A.K. Steib, M. Raducan, K. Karaghiosoff, P. Mayer, and P. Knochel Org. Lett. 13 2011 3182 3185
42. S.-S. Jin, H. Wang, and M.-H. Xu Chem. Commun. 47 2011 7230 7232
43. G. Chen, J. Gui, L. Li, and J. Liao Angew. Chem., Int. Ed. 50 2011 7681 7685
44. F. Xue, X. Li, and B. Wan J. Org. Chem. 76 2011 7256 7262
45. T.-S. Zhu, S.-S. Jin, and M.-H. Xu Angew. Chem., Int. Ed. 51 2012 780 783
46. H. Wang, T. Jiang, and M.-H. Xu J. Am. Chem. Soc. 135 2013 971 974
47. For chiral sulfur-alkene ligands developed by our group, see: X. Feng, Y. Wang, B. Wei, J. Yang, and H. Du Org. Lett. 13 2011 3300 3303
48. X. Feng, B. Wei, J. Yang, and H. Du Org. Biomol. Chem. 9 2011 5927 5929
49. Y. Wang, X. Feng, and H. Du Org. Lett. 13 2011 4954 4957
50. X. Feng, Y. Nie, J. Yang, and H. Du Org. Lett. 14 2012 624 627
51. Z. Liu, X. Feng, and H. Du Org. Lett. 14 2012 3154 3157
52. H. Venkatesan, M.C. Davis, Y. Altas, J.P. Snyder, and D.C. Liotta J. Org. Chem. 66 2001 3653 3661
53. Netz, A.; Oost, T.; Geneste, H.; Braje, W.; Unger, L.; Homberger, W.; Lubisch, W. PCT. No. PCT/EP2008/066933, 2008.