Catalytic asymmetric synthesis of substituted 3-hydroxy-2oxindoles

Angewandte Chemie - International Edition

Volumn 49, Issue 4, 2010, Pages 744-747

  Hanhan, Nadine V ^a   Sahin, Aziza H ^a   Chang, Toby W ^a   Fettinger, James C ^a   Franz, Annaliese K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Asymmetric catalysis; Heterocycles; Indium; Nucleophilic addition; Scandium

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL EQUATIONS; HETEROCYCLES; HIGH ENANTIOSELECTIVITY; HIGH YIELD; INDIUM COMPLEXES; NUCLEOPHILIC ADDITION; NUCLEOPHILIC ADDITIONS; OXINDOLES;

ADDITION REACTIONS; CATALYSIS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; INDIUM; SCANDIUM; SYNTHESIS (CHEMICAL);

SCANDIUM COMPOUNDS;

INDIUM; INDOLE DERIVATIVE; ISATIN; OXINDOLE; SCANDIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; INDIUM; INDOLES; ISATIN; MOLECULAR CONFORMATION; SCANDIUM; STEREOISOMERISM;

EID: 74849131136     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200904393     Document Type: Article

References (40)

1. a) Y. Kamano, H.-p. Zhang, Y. Ichihara, H. Kizu, K. Komiyama, G. R. Pettit, Tetrahedron Lett. 1995, 36, 2783-2784;
2. b) J. Kohno, Y. Koguchi, M. Nishio, K. Nakao, M. Kuroda, R. Shimizu, T. Ohnuki, S. Komatsubara, J. Org. Chem. 2000, 65, 990-995;
3. (c)Y.-Q. Tang, I. Sattler, R. Thiericke, S. Grabley, X.-Z. Feng, Eur. J. Org. Chem. 2001, 261 267;
4. (d)C.-Y. Gan, T.-S. Kam, Tetrahedron Lett. 2009, 50, 10591061.
5. a) T. Tokunaga, W. E. Hume, T. Umezome, K. Okazaki, Y. Ueki, K. Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji, H. Noguchi, R. Nagata,J Med. Chem. 2001, 44, 4641-4649;
6. b)T. Tokunaga, W. E. Hume, J. Nagamine, T. Kawamura, M. Taiji, R. Nagata, Bioorg. Med. Chem. Lett. 2005, 15, 1789-1792.
7. V. P. Kumar, V. P. Reddy, R. Sridhar, B. Srinivas, M. Narender, K. R. Rao, J. Org. Chem. 2008, 73, 1646-1648.
8. a) K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem. 2003, 115, 5647-5650;
9. Angew. Chem. Int. Ed. 2003, 42, 5489-5492;
10. b) R. Shintani, M. Inoue, T. Hayashi, Angew. Chem. 2006, 118, 3431-3434;
11. Angew. Chem. Int. Ed. 2006, 45, 3353-3356;
12. (c)P. Y. Toullec, R. B. C. Jagt, J. G. De Vries, B. L. Feringa, A. J. Minnaard, Org. Lett. 2006, 8, 2715-2718;
13. (d)D. Tomita, K. Yamatsugu, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 6946-6948;
14. e)H. Lai, Z. Huang, Q. Wu, Y. Qin, J. Org. Chem. 2009, 74, 283-288.
15. a) D. A. Klumpp, K. Y. Yeung, G. K. S. Prakash, G. A. Olah, J. Org. Chem. 1998, 63, 4481-4484;
16. b) J. S. Yadav, B. V. SubbaReddy, K. U. Gayathri, S. Meraj, A. R. Prasad, Synthesis 2006, 4121.-4123.
17. The formation of the 3,3'-bisindolyl oxindole product, most likely through formation of the indolenium ion, is enhanced for electron-rich nucleophiles.
18. a) D. A. Evans, K. R. Fandrick, H.-J. Song, K. A. Scheidt, R. Xu, J. Am. Chem. Soc. 2007, 729, 10029-10041;
19. b) G. Desimoni, G. Faita, M. Toscanini, M. Boiocchi, Chem. Eur. J. 2008, 14, 3630-3636;
20. (c)F. Zhao, H. Y. Tsui, P. J. Wu, J. Lu, T. P. Loh, J. Am. Chem. Soc. 2008, 130, 16492-16493.
21. The structure of the monoaddition product was confirmed by HRMS and the absolute configuration assigned on the basis of X-ray crystallography (anomalous dispersion method) of 3e, 3g, 31, 9, and 13. CCDC 749352 (3e), 749353 (3g), 749358 (31), 749355 (9), and 749356 (13) contain, the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif
22. a) T. Ishimaru, N. Shibata, J. Nagai, S. Nakamura, T. Toru, S. Kanemasa, J Am. Chem. Soc. 2006, 128, 16488-16489;
23. b) D. Sano, K. Nagata, T. Itoh, Org. Lett. 2008, 10, 1593-1595.
24. H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 6677.
25. When an aminophenol nucleophile was investigated, the reaction proceeded with a high background rate in the absence of a catalyst, so that no enantioselectivity was observed even, at lower temperatures.
26. a) V. Nair, S. Ros, C. N. Jayan, S. Viji, Synthesis 2003, 2542-2546;
27. b) G. Cravotto, G. B. Giovenzana, G. Palmisano, A. Penoni, T. Pilati,M. Sisti, F. Stazi, Tetrahedron: Asymmetry 2006,17, 3070-3074;
28. (c)J. Itoh, S. B. Han, M. J. Krische, Angew. Chem. 2009, 121, 6431-6434;
29. Angew. Chem. Int. Ed. 2009, 48, 6313-6316.
30. a) D. A. Evans, C. E. Masse, J. Wu, Org. Lett. 2002, 4, 3375-3378;
31. b) G. Luppi, P. G. Cozzi, M. Monari, B. Kaptein, Q. B. Broxterman, C. Tomasini, J. Org. Chem. 2005, 70, 7418-7421;
32. (c)T. Nakamura, S. Shirokawa, S. Hosokawa, A. Nakazaki, S. Kobayashi, Org. Lett. 2006, 8, 677-679;
33. (dJ.-R. Chen, X.-P. Liu, X.-Y. Zhu, L. Li, Y.-F. Qiao, J.-M. Zhang, W.-J. Xiao, Tetrahedron 2007, 63, 10437-10444;
34. e) A. V. Malkov, M. A. Kabeshov, M. Bella, O. Kysilka, D. A. Malyshev, K. Pluháčková, P. Kočovský, Org. Lett. 2007, 9, 5473-5476;
35. f)J.M. Ellis, L. E. Overman, H. R. Tanner, J. Wang, J. Org. Chem. 2008, 73, 9151 9154.
36. a) J. Lu, S.-J. Ji, Y.-C. Teo, T.-P. Loh, Org. Lett. 2005, 7, 159-161;
37. b) transmetalation of the allylic stannane to form an. allylic indium species is possible: M. Yasuda, M. Haga, A. Baba, Organometallics 2009, 28, 1998-2000.
38. S. Saaby, K. Nakama, M. A. Lie, R. G. Hazell, K. A. Jorgensen, Chem. Eur. J. 2003, 9, 6145-6154.
39. 3-pybox complex.
40. J. Comelles, A. Pericas, M. Moreno-Mañas, A. Vallribera, G. Drudis-Solé, A. Lledos, T. Parella, A. Roglans, S. GarcíaGranda, L. Roces-Fernández, J. Org. Chem. 2007, 72, 20772087.