Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins

Angewandte Chemie - International Edition

Volumn 45, Issue 20, 2006, Pages 3353-3356

  Shintani, Ryo ^a   Inoue, Mitsunori ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Boron; Isatins; Oxindoles; Rhodium

Indexed keywords

ARYL-BORONIC ACIDS; ASYMMETRIC CATALYSIS; ISATINS; OXINDOLES;

ALCOHOLS; BORON; CARBOXYLIC ACIDS; MOLECULAR STRUCTURE; RHODIUM; STEREOCHEMISTRY;

CATALYSIS;

ALKENE; BORONIC ACID DERIVATIVE; DRUG DERIVATIVE; HYDROCARBON; ISATIN; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; BORONIC ACIDS; CATALYSIS; HYDROCARBONS, CYCLIC; ISATIN; MODELS, CHEMICAL; RHODIUM; STEREOISOMERISM;

EID: 33746112742     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600392     Document Type: Article

References (48)

1. a) M. Somei, F. Yamada, Nat. Prod. Rep. 2003, 20, 216;
2. b) S. Hibino, T. Choshi, Nat. Prod. Rep. 2002, 19, 148;
3. c) 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, J. Morrone, J. Med. Chem. 1996, 39, 143;
4. d) Y. Koguchi, J. Kohno, M. Nishio, K. Takahashi, T. Okuda, T. Ohnuki, S. Komatsubara, J. Antibiot. 2000, 53, 105;
5. e) Y.-Q. Tang, I. Sattler, R. Thiericke, S. Grabley, X.-Z. Feng, Eur. J. Org. Chem. 2001, 261;
6. f) H. Suzuki, H. Morita, M. Shiro, J. Kobayashi, Tetrahedron 2004, 60, 2489.
7. 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;
8. b) J. Nagamine, R. Nagata, H. Seki, N. Nomura-Akimaru, Y. Ueki, K. Kumagai, M. Taiji, H. Noguchi, J. Endocrinol. 2001, 171, 481;
9. c) T. Tokunaga, W. E. Hume, J. Nagamine, T. Kawamura, M. Taiji, R. Nagata, Bioorg. Med. Chem. Lett. 2005, 15, 1789.
10. A. Di Malta, G. Garcia, R. Roux, B. Schoentjes, C. Serradeil-le Gal, B. Tonnerre, J. Wagnon, PCT Int. Appl. No. WO2003008407, 2003.
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, N. A. Meanwell, J. Med. Chem. 2002, 45, 1487.
12. There have been scattered examples of the preparation of enantiomerically enriched 3-aryl-3-hydroxy-2-oxindoles: a) by using an enantiopure substrate: S. Barroso, G. Blay, L. Cardona, I. Fernández, B. García, J. R. Pedro, J. Org. Chem. 2004, 69, 6821;
13. b) by using an enantiopure reagent: see Ref. [4];
14. c) through chiral HPLC resolution: see Ref. [2a].
15. For examples of the catalytic asymmetric preparation of 3-alkyl-3-hydroxy-2-oxindoles from isatins with moderate enantioselectivity, see: a) K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem. 2003, 115, 5529;
16. Angew. Chem. Int. Ed. 2003, 42, 5489 (76% ee);
17. b) G. Luppi, P. G. Cozzi, M. Monari, B. Kaptein, Q. B. Broxterman, C. Tomasini, J. Org. Chem. 2005, 70, 7418 (up to 77% ee).
18. For rhodium-catalyzed asymmetric phenylation of aldehydes, see: a) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475;
19. Angew. Chem. Int. Ed. 1998, 37, 3279;
20. b) K. Suzuki, S. Ishii, K. Kondo, T. Aoyama, Synlett 2006, 648.
21. Very recently, a rhodium-catalyzed asymmetric alkenylation of α-ketoesters was reported, see: J.-R. Kong, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 718.
22. For catalytic asymmetric addition of organozinc reagents to ketones, see: a) P. I. Dosa, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 445;
23. b) L. Pu, Tetrahedron 2003, 59, 9873;
24. c) J. M. Betancort, C. García, P. J. Walsh, Synlett 2004, 749;
25. d) D. J. Ramón, M. Yus, Angew. Chem. 2004, 116, 286;
26. Angew. Chem. Int. Ed. 2004, 43, 284.
27. For an example of a rhodium-catalyzed non-asymmetric addition of organotin reagents to activated ketones, see: S. Oi, M. Moro, H. Fukuhara, T. Kawanishi, Y. Inoue, Tetrahedron 2003, 59, 4351.
28. H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629.
29. a) Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, J. Am. Chem. Soc. 1998, 120, 5579;
30. b) T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052;
31. for reviews, see: c) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829;
32. d) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169.
33. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264.
34. a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614;
35. Angew. Chem. Int. Ed. Engl. 1993, 32, 566;
36. b) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769;
37. c) G. J. Dawson, C. G. Frost, J. M. J. Williams, S. J. Coote, Tetrahedron Lett. 1993, 34, 3149.
38. a) J.-G. Boiteau, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2003, 68, 9481;
39. b) B. L. Feringa, Acc. Chem. Res. 2000, 33, 346.
40. T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamamoto, M. Kumada, Bull. Chem. Soc. Jpn. 1980, 53, 1138.
41. a) T. Hayashi, Acc. Chem. Res. 2000, 33, 354;
42. b) Y. Uozumi, A. Tanahashi, S.-Y. Lee, T. Hayashi, J. Org. Chem. 1993, 58, 1945.
43. The reaction does not proceed in the absence of KOH.
44. The Flack parameter is 0.00(4) with this configuration (see Supporting Information for details): H. D. Flack, Acta Crystallogr. Sect. A 1983, 39, 876.
45. CCDC-293711 contains 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.
46. a) D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933;
47. b) P. Y. S. Lam, G. Vincent, C. G. Clark, S. Deudon, P. K. Jadhav, Tetrahedron Lett. 2001, 42, 3415;
48. c) G. C. H. Chiang, T. Olsson, Org. Lett. 2004, 6, 3079.