Regio- and stereoselective synthesis of 2-deoxy-C-aryl glycosides via palladium catalyzed decarboxylative reactions

Organic Letters

Volumn 13, Issue 17, 2011, Pages 4608-4611

  Xiang, Shaohua ^a   Cai, Shuting ^a   Zeng, Jing ^a   Liu, Xue Wei ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DECARBOXYLATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DECARBOXYLATION; GLYCOSIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 80052205630     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201820m     Document Type: Article

References (62)

1. Subadolnik, R. J. Nucleoside Antibiotics; Wiley-Interscience: New York, 1970.
2. Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1
3. Marquez, V. E.; Lim, M. I. Med. Res. Rev. 1986, 6, 1
4. Hansen, M. R.; Hurley, L. H. Acc. Chem. Res. 1996, 29, 249
5. Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407
6. Faulknew, D. J. Nat. Prod. Rep. 2000, 17, 7
7. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976
8. Horika, K.; Sakkurai, Y.; Nagasawa, M.; Hachiya, S.; Yonemitsu, O. Synlett 1994, 43
9. Paterson, L.; Kewon, L. E. Tetrahedron Lett. 1997, 38, 5727
10. Nicotra, F. Top. Curr. Chem. 1997, 187, 55
11. Qin, H.-L.; Lowe, J. T.; Panek, J. S. J. Am. Chem. Soc. 2007, 129, 38
12. Reddy, C. R.; Reddy, G. B.; Rao, C. L. Tetrahedron Lett. 2008, 49, 863
13. Bililign, T.; Griffith, B. R.; Thorson, J. S. Nat. Prod. Rep. 2005, 22, 742
14. Dubois, E.; Beau, J. M. Tetrahedron Lett. 1990, 31, 5165
15. Dubois, E.; Beau, J. M. J. Chem. Soc., Chem. Commun. 1990, 1191
16. Friesen, R. W.; Sturino, C. F. J. Org. Chem. 1990, 55, 2572
17. Dubois, E.; Beau, J. M. Carbohydr. Res. 1992, 228, 103
18. Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 72, 1262
19. Abas, A.; Beddoes, R. L.; Conway, J. C.; Quayle, P.; Urch, C. J. Synlett 1995, 1264
20. Steunenberg, P.; Jeanneret, V.; Zhu, Y.-H.; Vogel, P. Tetrahedron: Asymmetry 2005, 16, 337
21. Arai, I.; Lee, T. D.; Hanna, B.; Daves, G. D., Jr. Organometallics 1982, 1, 742
22. Cheng, J. C. Y.; Daves, G. D., Jr. Organometallics 1986, 5, 1753
23. Cheng, J. C. Y.; Hacksell, U.; Daves, G. D., Jr. J. Org. Chem. 1986, 51, 3093
24. Daves, G. D., Jr. Acc. Chem. Res. 1990, 23, 201
25. Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821
26. Moineau, C.; Bolitt, V.; Sinou, D. J. Org. Chem. 1998, 63, 582
27. Kaelin, D. E.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937
28. Steinhuebel, D. P.; Fleming, J. J.; Dubois, J. Org. Lett. 2002, 4, 293
29. Chen, C.-L.; Martin, S. F. Org. Lett. 2004, 6, 3581
30. Chen, C.-L.; Martin, S. F. J. Org. Chem. 2006, 71, 4810
31. Czernecki, S.; Dechavanne, V. Can. J. Chem. 1983, 61, 533
32. Benhaddou, R.; Czernecki, S.; Ville, G. J. Org. Chem. 1992, 57, 4612
33. Calimente, D.; Postema, M. H. D. J. Org. Chem. 1999, 64, 1770
34. Li, H.-H.; Ye, X.-S. Org. Biomol. Chem. 2009, 7, 3855
35. Lei, M.; Gao, L.; Yang, J. -S. Tetrahedron Lett. 2009, 50, 5135
36. Moral, J. A.; Moon, S.-J.; Rodriguez-Torres, S.; Minehan, T. Org. Lett. 2009, 11, 3734
37. Ramnauth, J.; Poulin, O.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2013
38. Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571
39. Figuera, N.; Frons, P.; Fernàndez, J.; Fiol, S.; Forner-Fernández, D.; Albericio, F. Tetrahedron Lett. 2005, 46, 7271
40. Xiong, D.-C.; Ye, X.-S.; Zhang, L. -H. Org. Lett. 2009, 11, 1709
41. Pan, D.; Jiao, N. Synlett 2010, 1577
42. Cheng, J. C. Y.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3083
43. Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250
44. Tanaka, D.; Myers, A. G. Org. Lett. 2004, 6, 433
45. Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323
46. Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
47. Goossen, L. J.; Rodríguez, N.; Melzer, B.; Linder, C.; Deng, J.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824
48. Goossen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043
49. Forgione, P.; Brochu, M. C.; Miguel, S. O.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350
50. Becht, J. M.; Catala, C.; Drian, C. L.; Wagner, A. Org. Lett. 2007, 9, 1781
51. Wang, C.-Y.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 4194
52. Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738
53. Hu, P.; Kan, J.; Su, W.-P.; Hong, M.-C. Org. Lett. 2009, 11, 2341
54. Lindh, J.; Sjöberg, P. J. R.; Larhed, M. Angew. Chem., Int. Ed. 2010, 49, 7733
55. Wang, C.-Y.; Rakshit, S.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 14006
56. Shang, R.; Yang, Z.-W.; Wang, Y.; Zhang, S.-L.; Liu, L. J. Am. Chem. Soc. 2010, 132, 14391
57. Lorpitthaya, R.; Xie, Z.-Z.; Kuo, J.-L.; Liu, X.-W. Chem.-Eur. J. 2008, 14, 1561
58. Sudibya, H. G.; Ma, J.-M.; Dong, X.; Ng, S.; Li, L.-J.; Liu, X.-W.; Chen, P. Angew. Chem., Int. Ed. 2009, 48, 2723
59. Zeng, J.; Vedachalam, S.; Xiang, S.-H.; Liu, X.-W. Org. Lett. 2011, 13, 42
60. Ding, F.-Q.; William, R.; Wang, F.; Ma, J.-M.; Ji, L.; Liu, X.-W. Org. Lett. 2011, 13, 652
61. Gorityala, B. K.; Ma, J.-M.; Pasunooti, K. K.; Cai, S.-T.; Liu, X.-W. Green Chem. 2011, 13, 573
62. Ding, F.-Q.; William, R.; Wang, S.-M.; Gorityala, B. K.; Liu, X.-W. Org. Biomol. Chem. 2011, 9, 3929