Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Lactols for de Novo Synthesis of Carbohydrate

Organic Letters

Volumn 17, Issue 21, 2015, Pages 5272-5275

  Wang, Hao Yuan ^a   Yang, Ka ^a   Yin, Dan ^a   Liu, Can ^a   Glazier, Daniel A ^a   Tang, Weiping ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; LACTONE; PALLADIUM;

ACYLATION; ALKYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; SYNTHESIS;

ACYLATION; ALKYLATION; CARBOHYDRATES; CATALYSIS; KINETICS; LACTONES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84946715090     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02641     Document Type: Article

References (60)

1. Ernst, B.; Magnani, J. L. Nat. Rev. Drug Discovery 2009, 8, 661 10.1038/nrd2852
2. Stallforth, P.; Lepenies, B.; Adibekian, A.; Seeberger, P. H. J. Med. Chem. 2009, 52, 5561 10.1021/jm900819p
3. Reina, J. J.; Bernardi, A. Mini-Rev. Med. Chem. 2012, 12, 1434 10.2174/138955712803832690
4. Wong, C.-H. Carbohydrate-based Drug Discovery; Wiley-VCH Verla: Weinheim, 2003.
5. Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A.; Sharpless, K. B.; Walker, F. J. Science 1983, 220, 949 10.1126/science.220.4600.949
6. Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Synthesis 1999, 1999, 341 10.1055/s-1999-3382
7. Harris, J. M.; Keranen, M. D.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2982 10.1021/jo990410+
8. Harris, J. M.; Keranen, M. D.; Nguyen, H.; Young, V. G.; O'Doherty, G. A. Carbohydr. Res. 2000, 328, 17 10.1016/S0008-6215(00)00031-8
9. Northrup, A. B.; MacMillan, D. W. C. Science 2004, 305, 1752 10.1126/science.1101710
10. Ahmed, M. M.; Berry, B. P.; Hunter, T. J.; Tomcik, D. J.; O'Doherty, G. A. Org. Lett. 2005, 7, 745 10.1021/ol050044i
11. Enders, D.; Grondal, C. Angew. Chem., Int. Ed. 2005, 44, 1210 10.1002/anie.200462428
12. Covell, D. J.; Vermeulen, N. A.; Labenz, N. A.; White, M. C. Angew. Chem., Int. Ed. 2006, 45, 8217 10.1002/anie.200603321
13. Han, S. B.; Kong, J. R.; Krische, M. J. Org. Lett. 2008, 10, 4133 10.1021/ol8018874
14. Aljahdali, A. Z.; Shi, P.; Zhong, Y.; O'Doherty, G. A. In Advances in Carbohydrate Chemistry and Biochemistry, Vol 69; Horton, D., Ed.; Elsevier: New York, 2013; Vol. 69, p 55.
15. Cuccarese, M. F.; Li, J. J.; O'Doherty, G. A. In Modern Synthetic Methods in Carbohydrate Chemistry: From Monosaccharides to Complex Glycoconjugates; Werz, D. B.; Vidal, S., Eds.; Wiley-VCH: Weinheim, 2014; p 1.
16. Demchenko, A. V. Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance; Wiley-VCH: Weinheim, 2008.
17. Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 1900 10.1002/anie.200802036
18. Li, X.; Zhu, J. J. Carbohydr. Chem. 2012, 31, 284 10.1080/07328303.2012.683910
19. McKay, M. J.; Nguyen, H. M. ACS Catal. 2012, 2, 1563 10.1021/cs3002513
20. Werz, D. B.; Vidal, S. Modern Synthetic Methods in Carbohydrate Chemistry: From Monosaccharides to Complex Glycoconjugates; Wiley-VCH: Weinheim, 2014.
21. Nokami, T. Yuki Gosei Kagaku Kyokaishi 2014, 72, 797 10.5059/yukigoseikyokaishi.72.797
22. Tsuji, J. Acc. Chem. Res. 1969, 2, 144 10.1021/ar50017a003
23. Trost, B. M. Acc. Chem. Res. 1980, 13, 385 10.1021/ar50155a001
24. Tsuji, J. Tetrahedron 1986, 42, 4361 10.1016/S0040-4020(01)87277-X
25. Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140 10.1021/ar00136a003
26. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921 10.1021/cr020027w
27. Kim, H.; Lee, C. Org. Lett. 2002, 4, 4369 10.1021/ol027104u
28. Kim, H.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 1336 10.1021/ja039746y
29. Comely, A. C.; Eelkema, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 8714 10.1021/ja0347538
30. Babu, R. S.; O'Doherty, G. A. J. Am. Chem. Soc. 2003, 125, 12406 10.1021/ja037097k
31. Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428 10.1021/ja039400n
32. Xiang, S.; Lu, Z.; He, J.; Hoang, K. L. M.; Zeng, J.; Liu, X.-W. Chem.-Eur. J. 2013, 19, 14047 10.1002/chem.201303241
33. Xiang, S.; He, J.; Tan, Y. J.; Liu, X.-W. J. Org. Chem. 2014, 79, 11473 10.1021/jo502078c
34. Xiang, S.; Hoang, K. L. M.; He, J.; Tan, Y. J.; Liu, X.-W. Angew. Chem., Int. Ed. 2014, 54, 604 10.1002/anie.201408739
35. Lim, W.; Kim, J.; Rhee, Y. H. J. Am. Chem. Soc. 2014, 136, 13618 10.1021/ja508587f
36. Achmatowicz, O.; Bukowski, P.; Szechner, B.; Zwierzchowska, Z.; Zamojski, A. Tetrahedron 1971, 27, 1973 10.1016/S0040-4020(01)98229-8
37. Achmatowicz, O., Jr.; Bukowski, P. Can. J. Chem. 1975, 53, 2524 10.1139/v75-359
38. Achmatowicz, O.; Szechner, B. Carbohydr. Res. 1976, 50, 23 10.1016/S0008-6215(00)84079-3
39. Bognar, R.; Herczegh, P. Carbohydr. Res. 1976, 52, 11 10.1016/S0008-6215(00)85941-8
40. Holder, N. L. Chem. Rev. 1982, 82, 287 10.1021/cr00049a003
41. van den Heuvel, M.; Cuiper, A. D.; van der Deen, H.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 1655 10.1016/S0040-4039(97)00155-X
42. Guo, H.; O'Doherty, G. A. Angew. Chem., Int. Ed. 2007, 46, 5206 10.1002/anie.200701354
43. Babu, R. S.; Chen, Q.; Kang, S.-W.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2012, 134, 11952 10.1021/ja305321e
44. Zhou, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 4339 10.1021/ol061683b
45. Wang, H.-y.; Yang, K.; Bennett, S. R.; Guo, S.-r.; Tang, W. Angew. Chem., Int. Ed. 2015, 54, 8756 10.1002/anie.201503151
46. Fu, G. C. Acc. Chem. Res. 2004, 37, 542 10.1021/ar030051b
47. Mueller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012 10.1002/anie.201006128
48. Taylor, J. E.; Bull, S. D.; Williams, J. M. J. Chem. Soc. Rev. 2012, 41, 2109 10.1039/c2cs15288f
49. Birman, V. B.; Li, X. M. Org. Lett. 2006, 8, 1351 10.1021/ol060065s
50. Li, X.; Jiang, H.; Uffman, E. W.; Guo, L.; Zhang, Y.; Yang, X.; Birman, V. B. J. Org. Chem. 2012, 77, 1722 10.1021/jo202220x
51. Yang, X.; Lu, G.; Birman, V. B. Org. Lett. 2010, 12, 892 10.1021/ol902969j
52. Lu, G.; Birman, V. B. Org. Lett. 2011, 13, 356 10.1021/ol102736t
53. Sheppard, C. I.; Taylor, J. L.; Wiskur, S. L. Org. Lett. 2011, 13, 3794 10.1021/ol2012617
54. Wang, L.; Akhani, R. K.; Wiskur, S. L. Org. Lett. 2015, 17, 2408 10.1021/acs.orglett.5b00919
55. Wu, X.; Li, X.; Zanotti-Gerosa, A.; Pettman, A.; Liu, J.; Mills, A. J.; Xiao, J. Chem.-Eur. J. 2008, 14, 2209 10.1002/chem.200701258
56. Croatt, M. P.; Carreira, E. M. Org. Lett. 2011, 13, 1390 10.1021/ol2000765
57. Ortiz, A.; Benkovics, T.; Beutner, G. L.; Shi, Z.; Bultman, M.; Nye, J.; Sfouggatakis, C.; Kronenthal, D. R. Angew. Chem., Int. Ed. 2015, 54, 7185 10.1002/anie.201502290
58. Shiina, I.; Nakata, K. Tetrahedron Lett. 2007, 48, 8314 10.1016/j.tetlet.2007.09.135
59. Shiina, I.; Nakata, K.; Ono, K.; Onda, Y.-s.; Itagak, M. J. Am. Chem. Soc. 2010, 132, 11629 10.1021/ja103490h
60. Nakata, K.; Gotoh, K.; Ono, K.; Futami, K.; Shiina, I. Org. Lett. 2013, 15, 1170 10.1021/ol303453j