The first preparation of 4-substituted 1,2-oxaborol-2(5H)-ols and their palladium-catalyzed cross-coupling with aryl halides to prepare stereodefined 2,3-disubstituted allyl alcohols

Synthesis

Volumn , Issue 7, 2006, Pages 1148-1154

  Fang, Guo Hua ^a   Yan, Zheng Jun ^a   Yang, Jun ^a   Deng, Min Zhi ^a  

^a Laboratory of Organometallic Chemistry Shanghai   (China)

Author keywords

Alkenylboronic acids; Copper catalyzed carbomagnesation; Disubstituted allyl alcohols; Stereodefined trisubstituted alkenes; Suzuki Miyaura cross coupling

Indexed keywords

CARBOXYLIC ACIDS; COPPER COMPOUNDS; HALOGEN COMPOUNDS; PALLADIUM COMPOUNDS;

ALKENYLBORONIC ACIDS; COPPER-CATALYZED CARBOMAGNESATION; DISUBSTITUTED ALLYL ALCOHOLS; STEREODEFINED TRISUBSTITUTED ALKENES; SUZUKI-MIYAURA CROSS-COUPLING;

ALCOHOLS;

1,2 OXABOROL 2(5H) OL DERIVATIVE; ALCOHOL DERIVATIVE; ALKENYL GROUP; ALLYL ALCOHOL; BORONIC ACID DERIVATIVE; CARBON; COPPER; HALIDE; MAGNESIUM; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPARGYL ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; STEREOCHEMISTRY; SUZUKI MIYAURA CROSS COUPLING REACTION; SYNTHESIS;

EID: 33645969615     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926388     Document Type: Article

References (53)

1. Cross-coupling reactions: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
2. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
3. Asymmetric Mannich reactions: (c) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.
4. (d) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
5. Asymmetric 1, 2- or 1, 4-additions: (e) Hyuga, S.; Hara, S.; Suzuki, A. Bull. Chem. Soc. Jpn. 1992, 65, 2303.
6. (f) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229.
7. (g) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem. Int. Ed. 1998, 37, 3279.
8. (h) Halo-boron exchange: Petasis, N. A.; Zavialov, I. A. Tetrahedron Lett. 1996, 37, 567.
9. Asymmetric cyclopropanation reactions: (i) Fontain, P.; Carboni, B.; Vaultier, M.; Carie, R. Tetrahedron Lett. 1989, 30, 4815.
10. (j) Imai, T.; Maineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986.
11. (k) Diels-Alder reactions: Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450.
12. Ullmann reaction: (l) Chan, D. M. T.; Monaco, K. L.; Wang, R. P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
13. (m) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
14. (n) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
15. (o) Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400; and references therein.
16. (a) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988.
17. (b) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083.
18. Deloux, L.; Srebnik, M. J. Org. Chem. 1994, 59, 6871.
19. Advances in Boron Chemistry; Siebert, W., Ed.; RSC: London, 2000.
20. (a) Li, J.; Xu, H.; Zhang, Y. M. Tetrahedron Lett. 2005, 46, 1931.
21. (b) Das, B.; Banerjee, J.; Majhi, A.; Mahender, G. Tetrahedron Lett. 2004, 45, 9225.
22. (c) Genin, E.; Michelet, V.; Genet, J.-P. J. Organomet. Chem. 2004, 689, 3820.
23. (d) Cai, M.-Z.; Ye, H.-D.; Zhao, H.; Song, C.-S. J. Chem. Res., Synop. 2003, 8, 465.
24. (e) Das, B.; Banerjee, J.; Mahender, G.; Majhi, A. Org. Lett. 2004, 6, 3349.
25. (f) Li, J.; Qian, W.-X.; Zhang, Y.-M. Tetrahedron 2004, 60, 5793.
26. (g) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939.
27. (h) Fürstner, A.; Thiel, O. R.; Ackermann, L. Org. Lett. 2001, 3, 449.
28. (i) Tago, K.; Kogen, H. Org. Lett. 2000, 2, 1975.
29. (a) Yu, S.; Li, N. S.; Kabalka, G. W. J. Org. Chem. 1999, 64, 5822.
30. (b) Havranek, M.; Dvorak, D. J. Org. Chem. 2002, 67, 2125; and references therein.
31. Broene, R. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 12569.
32. Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M.-C; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 9870.
33. Murphy, J. A.; Patterson, C. W. J. Chem. Soc., Perkin Trans. 1 1993, 405.
34. (a) Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791.
35. (b) Srikrishna, A.; Kumar, P. P.; Viswajanani, R. Tetrahedron Lett. 1996, 37, 1683.
36. (a) Havranek, M.; Dvorak, D. Collect. Czech. Chem. Commun. 2000, 65, 434.
37. (b) Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem. 1979, 168, 1.
38. (c) Spino, C.; Godbout, C.; Beaulieu, C.; Harter, M.; Mwene-Mbeja, T. M.; Boisvert, L. J. Am. Chem. Soc. 2004, 126, 13312 .
39. (d) Wong, T.; Tjepkema, M. W.; Audrain, H.; Wilson, P. D.; Fallis, A. G. Tetrahedron Lett. 1996, 37, 755.
40. (e) Forgione, P.; Fallis, A. G. Tetrahedron Lett. 2000, 41, 11.
41. (a) Urawa, Y.; Ogura, K. Tetrahedron Lett. 2002, 44, 271.
42. (b) Haddach, M.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 3109.
43. (c) Gooben, L. J.; Ghosh, K. Eur. J. Org. Chem. 2002, 3254.
44. (d) Kakino, R.; Yasumi, S.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137.
45. (e) Gooben, L. J.; Ghosh, K. Angew. Chem. Int. Ed. 2001, 40, 3458.
46. (f) Lei, A.-W.; Zhang, X.-M. Tetrahedron Lett. 2002, 43, 2525.
47. (g) Liu, X.-X.; Deng, M.-Z. Chem. Commun. 2002, 6, 622.
48. (h) Netherton, M. R.; Dai, C.; Neuschutz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
49. (i) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 23, 2408.
50. (a) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
51. (b) Littke, A F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
52. (c) Yin, J. J.; Rainka, M. P.; Zhang, X. X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
53. (d) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290; and references therein.