Synthesis of optically active 1,4-benzoxazine derivatives using palladium-catalyzed coupling kinetic resolution

Tetrahedron Asymmetry

Volumn 22, Issue 9, 2011, Pages 948-954

  Koteshwar Rao, R ^a   Sekar, Govindasamy ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; 1,4 BENZOXAZINE DERIVATIVE; 12 TOSYL 6,7,10,11,11A,12 HEXAHYDRO 5AH BENZO[B]CYCLOOCTA[E][1,4]OXAZINE; 3A,9A 7 METHOXY 9 TOSYL 1,2,3,3A,9,9A HEXAHYDROBENZO[B]CYCLOPENTA[E][1,4]OXAZINE; 3A,9A 9 TOSYL 1,2,3,3A,9,9A HEXAHYDROBENZ O [B]CYCLOPENTA[E][1,4]OXAZINE; 4A,10A 10 TOSYL 2,3,4,4A,10,10A HEXAHYDRO 1H PHENOXAZINE; 4A,10A 8 CHLORO 10 TOSYL-2,3,4,4A,10,10A HEXAHYDRO 1H PHENOXAZINE; 4A,10A 8 PHENYL 10 TOSYL 2,3,4,4A,10,10A HEXAHYDRO 1H PHENOXAZINE; 7 METHYL 9 TOSYL 1,2,3,3A,9,9A HEXAHYDROBENZO[B]CYCLOPENTA[E][1,4]OXAZINE; 8 METHOXY 10 TOSYL 2,3,4,4A,10,10A HEXAHYDRO 1H PHENOXAZINE; [8 (2 BROMO 4 PHENOXY)CYCLOOCT 4 ENYL] 4 METHYLBENZENESULFONAMIDE; N [2 (2 BROMO 4 CHLOROPHENOXY)CYCLOHEXYL] 4 METHYLBENZENESULFONAMIDE; N [2 (2 BROMO 4 METHOXYPHENOXY) CYCLOHEXYL] 4 METHYLBENZENESULFONAMIDE; N [2 (2 BROMO 4 METHOXYPHENOXY)CYCLOPENT YL] 4 METHYLBENZENESULFONAMIDE; N [2 (2 BROMO 4 METHYLPHENOXY)CYCLOPENTYL] 4 METHYLBENZENESULFONAMIDE; N [2 (2 BROMOPHENOXY)CYCLOHEXYL] 4 METHYLBENZENESULFONAMIDE; N [2 (2 BROMOPHENOXY)CYCLOPENTYL] 4 METHYLBENZENESULFONAMIDE; N [2 (3 BROMOBIPHENYL 4 YLOXY)CYCLOHEXYL] 4 METHYLBENZENESULFONAMIDE; OXAZINE DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL RESOLUTION; PALLADIUM CATALYZED COUPLING KINETIC RESOLUTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 79960931275     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.06.005     Document Type: Article

References (34)

1. (a) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer, 1999;
2. (b) Ojima, I. Catalytic Asymmetric Synthesis; Wiley, 2000;
3. (c) Noyori, R. Adv. Synth. Catal. 2003, 345, 15;
4. (d) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483;
5. (e) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520.
6. (a) Hartwig, J. F. Nature 2008, 455, 314;
7. (b) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041;
8. (c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046;
9. (d) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428;
10. (e) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400;
11. (f) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337;
12. (g) Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973.
13. (a) Bourlot, A-S.; Sánchez, I.; Dureng, G.; Guillaumet, G.; Massingham, R.; Monteil, A.; Winslow, E.; Pujol, M. D.; Mérour, J.-Y. J. Med. Chem. 1998, 41, 3142;
14. (b) Combs, D. W.; Rampulla, M. S.; Bell, S. C.; Klaubert, D. H.; Tobia, A. J.; Falotico, R.; Haertlein, R. B.; Lakas-Weiss, C.; Moore, C. J. B. J. Med. Chem. 1990, 33, 380;
15. (c) D'Ambra, E. T.; Estep, G. K.; Bell, R. M.; Eissenstat, A. M.; Josef, A. K.; Ward, J. S.; Haycock, A. D.; Baizman, R. E.; Casiano, M. F.; Beblin, C. N.; Chippari, M. S.; Greo, D. J.; Kullnig, K. R.; Daley, T. G. J. Med. Chem. 1992, 35, 124;
16. (d) Largeron, M.; Dupuy, H.; Fleury, M. B. Tetrahedron 1995, 51, 4953.
17. Kuroita, T.; Sakamori, M.; Kawakita, T. Chem. Pharm. Bull. 1996, 44, 756.
18. Butler, R.; Chapleo, C. B.; Myers, P. L.; Welbourn, A. P. J. Heterocycl. Chem. 1985, 177.
19. Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Takayama, K.; Yoden, T.; Uchida, W.; Asano, M.; Fujita, S.; Yanagisawa, I.; Fujikura Chem. Pharm. Bull. 1996, 44, 103.
20. Albanese, D.; Landini, D.; Lupi, V.; Penso, M. Ind. Eng. Chem. Res. 2003, 42, 680.
21. Brown, D. W.; Ninan, A.; Sainsbury, M. Synthesis 1997, 895.
22. (a) Naidu, A. B.; Raghunath, O. R.; Prasad, D. J. C.; Sekar, G. Tetrahedron Lett. 2008, 49, 1057;
23. (b) Naidu, A. B.; Sekar, G. Tetrahedron Lett. 2008, 49, 3147;
24. (c) Naidu, A. B.; Jaseer, E. A.; Sekar, G. J. Org. Chem. 2009, 74, 3675;
25. (d) Prasad, D. J. C.; Sekar, G. Org. Biomol. Chem. 2009, 7, 5091.
26. Koteshwar Rao, R.; Naidu, A. B.; Sekar, G. Org. Lett. 2009, 11, 1923.
27. For information on Kinetic Resolution, see: (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974;
28. (b) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936;
29. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5;
30. (d) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794;
31. (e) Wolf, C. Dynamic Stereochemistry of Chiral Compounds; RSC, 2008.
32. (a) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149;
33. (b) Chianese, A. R.; Crabtree, R. H. Organometallics 2005, 24, 4432.
34. Kagan, H. B.; Fiaud, J. C. In Topics in Stereochemistry; Wiley: New York, 1988; Vol. 18, p 249.