Oxazaborolidinone-catalyzed alkylative ring-opening reaction of cyclic anhydrides with methallylstannane

Synthesis

Volumn , Issue 15, 2006, Pages 2483-2488

  Suzuki, Jun ^a   Harada, Toshiro ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric catalysis; Boron; Carboxylic acids; Lewis acid; Ring opening

Indexed keywords

BORON; CARBOXYLIC ACIDS; CATALYSIS; REACTION KINETICS;

ANHYDRIDES; ASYMMETRIC CATALYSIS; LEWIS ACIDS; RING OPENING;

ORGANIC COMPOUNDS;

3 METHYLBUT 3 ENOYL CARBOXYLIC ACID; ACETYLCARBOXYLIC ACID DERIVATIVE; ACID ANHYDRIDE; CARBOXYLIC ACID DERIVATIVE; METHALLYLSTANNANE; OXAZABOROLIDINE DERIVATIVE; OXAZABOROLIDINONE DERIVATIVE; TIN DERIVATIVE; TIN HYDRIDE; TRIBUTYLMETHALLYLSTANNANE; UNCLASSIFIED DRUG;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; ASYMMETRIC CATALYSIS; RING OPENING;

EID: 33747176815     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942473     Document Type: Article

References (55)

1. (a) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1.
2. (b) Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
3. (c) Hoffman, R. W. Angew. Chem. Int. Ed. 2003, 42, 1096.
4. (a) Spivey, A. C.; Andrews, B. I. Angew. Chem. Int. Ed. 2001, 40, 3131.
5. (b) Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965.
6. (c) Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
7. (a) Hiratake, J.; Yamamoto, Y.; Oda, J. J. Chem. Soc., Chem. Commun. 1985, 1717.
8. (b) Hiratake, J.; Inagaki, M.; Yamamoto, Y.; Oda, J. J. Chem. Soc., Perkin Trans. 1 1987, 1053.
9. (c) Aitken, R. A.; Gopal, J.; Hirst, J. A. J. Chem. Soc., Chem. Commun. 1988, 632.
10. (d) Aitken, R. A.; Gopal, J. Tetrahedron: Asymmetry 1990, 1, 517.
11. (e) Bolm, C.; Gerlach, A.; Dinter, C. Synlett 1999, 195.
12. (f) Bolm, C.; Schiffers, I.; Dinter, C. L.; Gerlach, A. J. Org. Chem. 2000, 65, 6984.
13. (g) Chen, Y.; Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2000, 122, 9542.
14. (h) Honjo, T.; Sano, S.; Shiro, M.; Nagao, Y. Angew. Chem. Int. Ed. 2005, 44, 5838.
15. For Lewis acid catalyzed asymmetric desymmetrization with alkoxide nucleophiles, see: (a) Shimizu, M.; Matsukawa, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1993, 66, 2128.
16. (b) Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
17. (c) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710.
18. (d) Seebach, D.; Jaeschke, G.; Gottewald, K.; Matsuda, K.; Formisano, R.; Chaplin, D. A. Tetrahedron 1997, 53, 7539.
19. (e) Jaeschke, G.; Seebach, D. J. Org. Chem. 1998, 63, 1190.
20. (a) Real, S. D.; Kronenthal, D. R.; Wu, H. Y. Tetrahedron Lett. 1993, 34, 8063.
21. (b) Shintani, R.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 1057.
22. (a) Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 174.
23. (b) Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 10248.
24. (a) Takasu, M.; Yamamoto, H. Synlett 1990, 194.
25. (b) Sartor, D.; Saffrich, J.; Helmchen, G. Synlett 1990, 197.
26. (c) Kiyooka, S.-I.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276.
27. (d) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966.
28. (e) For leading references, see: Ishihara K., Kondo S., Yamamoto H.; J. Org. Chem.; 2000, 65: 9125.
29. (a) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101.
30. (b) Wang, X.; Harada, T.; Iwai, H.; Oku, A. Chirality 2003, 15, 28.
31. (c) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, K.; Fujita, M.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046.
32. (d) Harada, T.; Adachi, S.; Wang, X. Org. Lett. 2004, 6, 4877.
33. (e) Harada, T.; Yamamoto, Y.; Kusukawa, T. Chem. Commun. 2005, 859.
34. (f) Harada, T.; Yamauchi, T.; Adachi, S. Synlett 2005, 2151.
35. (g) Singh, R. S.; Harada, T. Eur. J. Org. Chem. 2005, 3433.
36. (a) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
37. (b) Harada, T.; Egusa, T.; Oku, A. Tetrahedron Lett. 1998, 39, 5535.
38. (c) Harada, T.; Egusa, T.; Kinugasa, M.; Oku, A. Tetrahedron Lett. 1998, 39, 5531.
39. (d) Kinugasa, M.; Harada, T.; Oku, A. Tetrahedron Lett. 1998, 39, 4523.
40. (e) Harada, T.; Nakamura, T.; Kinugasa, M.; Oku, A. Tetrahedron Lett. 1999, 40, 503.
41. (f) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 61.
42. (g) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309.
43. (h) Harada, T.; Imai, K.; Oku, A. Synlett 2002, 972.
44. (i) Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080.
45. (j) Harada, T.; Shiraishi, K. Synlett 2005, 1999.
46. Harada, T.; Nakamura, T.; Kinugasa, M.; Oku, A. J. Org. Chem. 1999, 64, 7594.
47. (a) Santelli-Rouvier, C. Tetrahedron Lett. 1984, 25, 4371.
48. (b) Pellissier, H.; Wilmouth, S.; Santelli, M. Bull. Soc. Chim. Fr. 1995, 132, 637.
49. (c) Michaut, M.; Santelli, M.; Parrain, J.-L. J. Organomet. Chem. 2000, 606, 93.
50. Gauthier, D. R. Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
51. Corey, E. J.; Yu, C.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495.
52. (a) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Chem. Lett. 1986, 1857.
53. (b) Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954.
54. Kinugasa, M.; Harada, T.; Egusa, T.; Fujita, K.; Oku, A. Bull. Chem. Soc. Jpn. 1996, 69, 3639.
55. Haubold, W.; Herdtle, J.; Gollinger, W.; Einholz, W. J. Organomet. Chem. 1986, 315, 1.