Grignard addition to imines derived from isatine: A method for the asymmetric synthesis of quaternary 3-aminooxindoles

Journal of Organic Chemistry

Volumn 74, Issue 12, 2009, Pages 4537-4541

  Lesma, Giordano ^a   Landoni, Nicola ^a   Pilati, Tullio ^b   Sacchetti, Alessandro ^c   Silvani, Alessandra ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

^c POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ALKENYL; ASYMMETRIC SYNTHESIS; CHEMICAL EQUATIONS; DEPROTECTION; GRIGNARD ADDITION; GRIGNARD REAGENT; REACTION PRODUCTS; SYNTHETIC TRANSFORMATIONS;

CHEMICAL REACTIONS;

NITROGEN COMPOUNDS;

3 [2 (TERT BUTYLDIMETHYLSILYOXY) 1 PHENYLETHYLIMINO) 1 (4 METHOXYBENZYL)INDOLIN 2 ONE 6; 3 ALLYL 3 [2 (TERT BUTYLDIMETHYLSILYOXY) 1 PHENYLETHYLAMINO] 1 (4 METHOXYBENZYL)INDOLIN 2 ONE; 3 ALLYL 3 AMINO 1 (4 METHOXYBENZYL)INDOLIN 2 ONE; GRIGNARD REAGENT; IMINE; INDOLE DERIVATIVE; N[1 (4 METHOXYBENZYL) 2 OXOINDOLIN 3 YLIDENE] 2 METHYLPROPANE 2 SULFINAMIDE 8; N[3 ALLYL 1 (4 METHOXYBENZYL) 2 OXOINDOLIN 3 YL] 2 METHYLPROPANE 2 SULFINAMIDE; TERT BUTYL 3 [2 (TERT BUTYLDIMETHYLSILYOXYL) 1 PHENYLETHYLAMINO] 3 HYDROXY 2 OXOINDOLINE 1 CARBOXYLATE 7; TERT BUTYL 3 ALLYL 3 [2 (TERT BUTYLDIMETHYLSILYOXY) 1 PHENYLETHYLAMINO] 2 OXOINDOLINE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; DEPROTECTION REACTION; DRUG SYNTHESIS; GRIGNARD REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM;

IMINES; INDOLES; QUATERNARY AMMONIUM COMPOUNDS; STEREOISOMERISM;

EID: 67249129306     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900623c     Document Type: Article

References (49)

1. (a) Netz, A.; Oost, T.; Geneste, H.; Braje, W. M.; Wernet, W.; Unger, L.; Hornberger, W.; Lubisch, W. PTC Int. Appl. WO 2008080971, 2008.
2. b) Chen, L.; Zhang, J.; Zhang, Z.; Yang, S. PTC Int. Appl. WO2008034736, 2008.
3. (c) Stevens, F. C.; Bloomquist, W. E.; Borel, A. G.; Cohen, M. L.; Droste, C. A.; Heima, M. L.; Kriaciunas, A.; Sall, D. J.; Tinsley, F. C.; Jesudason, C. D. Bioorg. Med. Chem. Lett. 2007, 17, 6270-6273.
4. (d) Shanmugam, P.; Viswambharan, B.; Madhavan, S. Org. Lett. 2007, 9, 4095-4098.
5. (e) Ghosh, A. K.; Schiltz, G.; Perali, R. S.; Leshchenko, S.; Kay, S.; Walters, D. E.; Koh, Y.; Maeda, K.; Mitsuya, H. Bioorg. Med. Chem. Lett. 2006, 16, 1869-1873.
6. (f) Suzuki, H.; Morita, H.; Shiro, M.; Kobayashi, J. Tetrahedron 2004, 60, 2489-2495.
7. (g) Somei, M.; Yamada, F. Nat. Prod. Rep. 2003, 20, 216-242.
8. (h) Tang, Y.-Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X.-Z. Eur. J. Org. Chem. 2001, 261-267.
9. Ochi, M.; Kawasaki, K.; Kataoka, H.; Uchio, Y. Biochem. Biophys. Res. Commun. 2001, 283, 1118.
10. (a) Decaux, G.; Soupart, A.; Vassart, G. Lancet 2008, 371, 1624-1632.
11. (b) Shimazaki, T.; Iijima, M.; Chaki, S. Eur. J. Pharmacol. 2006, 543, 63-67.
12. (c) Bernard, K.; Bogliolo, S.; Ehrenfeld, J Br. J. Pharmacol. 2005, 144, 1037.
13. (a) Nielsen, P. H.; Anthoni, U.; Christophersen, C. Acta Chem. Scand. 1988, B42, 489.
14. (b) Anthoni, U.; Chevolot, L.; Larsen, C.; Nielsen, P. H.; Christophersen, C. J. Org. Chem. 1987, 52, 4709.
15. (c) Chevolot, L.; Chevolot, A.-M.; Gajhede, M.; Larsen, C.; Anthoni, U.; Christophersen, C. J. Am. Chem. Soc. 1985, 107, 4542.
16. (a) Yasui, Y.; Kamisaki, H.; Takemoto, Y. Org. Lett. 2008, 10, 3303-3306.
17. (b) Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008, 10, 3583-3586.
18. (c) Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748-8758.
19. (d) Gademann, K.; Bonazzi, S. Angew. Chem., Int. Ed. 2007, 46, 5656-5658.
20. (e) Cravotto, G.; Giovenzana, G. B.; Palmisano, G.; Penoni, A.; Pilati, T. Tetrahedron: Asymmetry 2006, 17, 3070-3074.
21. (f) Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209-2219.
22. (g) Dounay, A. B.; Hatanaka, K.; Kodanko, J. J.; Oestreich, M.; Overman, L. E.; Pfeifer, L. A.; Weiss, M. M. J. Am. Chem. Soc. 2003, 125, 6261-6271.
23. (a) Jia, Y.-X.; Hillgren, J. M.; Watson, M. L.; Marsden, S. P.; Kündig, E. P. Chem. Commun. 2008, 4040-4042.
24. (b) Marsden, S. P.; Watson, M. L.; Raw, S. A. Org. Lett. 2008, 10, 2905-2908.
25. Emura, T.; Eseki, T.; Tachibana, K.; Shimizu, M. J. Org. Chem. 2006, 71, 8559.
26. For revisions of organometallic additions to imines, see: (a) Ding, H.; Friestad, G. K. Synthesis 2005, 2815-2829, and references cited therein.
27. (b) Alvaro, G.; Savoia, D. Synlett 2002, 651-673.
28. (c) Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
29. (a) Vilaivan, T.; Bhanthumnavin, W.; Sritana-Anant, Y. Curr. Org. Chem. 2005, 9, 1315-1392.
30. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
31. For (R)-phenylglycinol, see: (a) Fustero, S.; Sánchez- Roselló, M.; Rodrigo, V.; del Pozo, C.; Sanz-Cervera, J. F.; Simón, A. Org. Lett. 2006, 8, 4129-4132.
32. (b) Chaume, G.; Van Severen, M.-C.; Marinkovic, S.; Brigaud, T. Org. Lett. 2006, 8, 6123-6126.
33. (c) Spero, D. M.; Kapadia, S. R. J. Org. Chem. 1997, 62, 5537-5541.
34. For (R)-tert-butanesulfinamide, see: (d) Rech, J. C.; Yato, M.; Duckett, D.; Ember, B.; LoGrasso, F. V.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 490-491.
35. (e) Denolf, B.; Mangelinckx, S.; Törnroos, K. W.; De Kimpe, N. Org. Lett. 2006, 8, 3129-3132.
36. (f) Lanter, J. C.; Chen, H.; Zhang, X.; Sui, Z. Org. Lett. 2005, 7, 5905-5907.
37. (g) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641-6643.
38. (h) McMahon, J. P.; Ellman, J. A. Org. Lett. 2004, 6, 1645-1647.
39. (i) Shaw, A. W.; deSolms, S. J. Tetrahedron Lett. 2001, 42, 7173-7176.
40. (j) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396-3397.
41. Vine, K. L.; Locke, J. M.; Ranson, M.; Pyne, S. G.; Bremner, J. B. J. Med. Chem. 2007, 50, 5109-5117.
42. Wille, G.; Steglich, W. Synthesis 2001, 759-762.
43. Miller, S. A.; Chamberlin, A. R. J. Org. Chem. 1989, 54, 2502-2504.
44. Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772-8778.
45. (a) Steinig, A. G.; Spero, D. M. J. Org. Chem. 1999, 64, 2406-2410.
46. (b) Spero, D. M.; Kapadia, S. R. J. Org. Chem. 1997, 62, 5537-5541.
47. (a) Denolf, B.; Mangelinckx, S.; Törnroos, K. W.; De Kimpe, N. Org. Lett. 2007, 9, 187-190.
48. (b) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051-2054.
49. This product was prepared according to the procedure reported in: Palomo, C.; Aizpurua, J. M.; Balentová, E.; Jimenez, A.; Oyarbide, J.; Fratila, R. M.; Miranda, J. I. Org. Lett. 2007, 9, 101-104.