Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ

Tetrahedron

Volumn 71, Issue 8, 2015, Pages 1187-1191

  Jiang, Shan Shan ^a   Gu, Bo Qi ^a   Zhu, Ming Yu ^a   Yu, Xingxin ^a   Deng, Wei Ping ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Allylic alcohols; Kinetic resolution; Nucleophilic catalyst

Indexed keywords

ALLYL ALCOHOL; NUCLEOPHILE; PROPIONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENZYME KINETICS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 84922135499     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.01.018     Document Type: Article

References (60)

1. S. France, D.J. Guerin, S.J. Miller, and T. Lectka Chem. Rev. 103 2003 2985 3012
2. E. Vedejs, and M. Jure Angew. Chem., Int. Ed. 44 2005 3974 4001
3. R.P. Wurz Chem. Rev. 107 2007 5570 5595
4. A.C. Spivey, and S. Arseniyadis Top. Curr. Chem. 291 2010 233 280
5. H. Pellissier Adv. Synth. Catal. 353 2011 1613 1666
6. C.E. Müller, and P.R. Schreiner Angew. Chem., Int. Ed. 50 2011 6012 6042
7. E. Vedejs, O. Daugulis, and S.T. Diver J. Org. Chem. 61 1996 430 431
8. E. Vedejs, and X.H. Chen J. Am. Chem. Soc. 118 1996 1809 1810
9. J.C. Ruble, H.A. Latham, and G.C. Fu J. Am. Chem. Soc. 119 1997 1492 1493
10. J.C. Ruble, J. Tweddell, and G.C. Fu J. Org. Chem. 63 1998 2794 2795
11. G.C. Fu Acc. Chem. Res. 33 2000 412 420
12. V.B. Birman, E.W. Uffman, J. Hui, X.M. Li, and C.J. Kilbane J. Am. Chem. Soc. 126 2004 12226 12227
13. V.B. Birman, and H. Jiang Org. Lett. 7 2005 3445 3447
14. V.B. Birman, and X. Li Org. Lett. 8 2006 1351 1354
15. V.B. Birman, and X. Li Org. Lett. 10 2008 1115 1118
16. Y. Zhang, and V.B. Birman Adv. Synth. Catal. 351 2009 2525 2529
17. T. Kawabata, M. Nagato, K. Takasu, and K. Fuji J. Am. Chem. Soc. 119 1997 3169 3170
18. E. Vedejs, and O. Daugulis J. Am. Chem. Soc. 121 1999 5813 5814
19. A.C. Spivey, T. Fekner, and S.E. Spey J. Org. Chem. 65 2000 3154 3159
20. G. Naraku, N. Shimomoto, T. Hanamoto, and J. Inanaga Enantiomer 5 2000 135 138
21. G.T. Copeland, and S.J. Miller J. Am. Chem. Soc. 123 2001 6496 6502
22. K.-S. Jeong, S.-H. Kim, H.-J. Park, K.-J. Chang, and K.S. Kim Chem. Lett. 2002 1114 1115
23. G. Priem, B. Pelotier, S.J.F. Macdonald, M.S. Anson, and I.B. Campbell J. Org. Chem. 68 2003 3844 3848
24. G.C. Fu Acc. Chem. Res. 37 2004 542 547
25. D. Terakado, H. Koutaka, and T. Oriyama Tetrahedron: Asymmetry 16 2005 1157 1165
26. S. Yamada, T. Misono, and Y. Iwai Tetrahedron Lett. 46 2005 2239 2242
27. D. Diez, M.J. Gil, R.F. Moro, and N.M. Garrido Tetrahedron: Asymmetry 16 2005 2980 2985
28. S.J. Connon, C.O. Dalaigh, S.J. Hynes, and D.J. Maher Org. Biomol. Chem. 3 2005 981 984
29. S. Mizuta, Y. Ohtsubo, T. Tsuzuki, T. Fujimoto, and I. Yamamoto Tetrahedron Lett. 47 2006 8227 8229
30. H.V. Nguyen, M. Motevalli, and C.J. Richards Synlett 2007 725 728
31. E.P. Kündig, A.E. Carcia, T. Lomberget, P.P. Garcia, and P. Romanens Chem. Commun. 2008 3519 3521
32. C.K. De, E.G. Klauber, and D. Seidel J. Am. Chem. Soc. 131 2009 17060 17061
33. R. Hrdina, C.E. Müller, and P.R. Schreiner Chem. Commun. 2010 2689 2690
34. D.R. Carbery, M.R. Crittall, and H.S. Rzepa Org. Lett. 13 2011 1250 1253
35. B. Hu, M. Meng, Z. Wang, W. Du, J.S. Fossey, X. Hu, and W.-P. Deng J. Am. Chem. Soc. 132 2010 17041 17044
36. B. Hu, M. Meng, J.S. Fossey, W. Mo, X. Hu, and W.-P. Deng Chem. Commun. 2011 10632 10634
37. Z. Wang, J. Ye, R. Wu, Y.-Z. Liu, J.S. Fossey, J. Cheng, and W.-P. Deng Catal. Sci. Technol. 4 2014 1909 1913
38. S. Jiang, B. Hu, X. Yu, and W. Deng Chin. J. Chem. 32 2014 694 698
39. T. Katsuki, and K.B. Sharpless J. Am. Chem. Soc. 102 1980 5974 5976
40. J.M. Brown, and R.G. Naik J. Chem. Soc., Chem. Commun. 1982 348 350
41. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765 5780
42. K. Burgess, and L.D. Jennings J. Am. Chem. Soc. 113 1991 6129 6139
43. R.S. Atkinson, S. Ulukanli, and P.J. Williams J. Chem. Soc., Perkin Trans. 1 1999 2121 2128
44. K. Bogár, P.H. Vidal, A.R.A. León, and J.-E. Bäckvall Org. Lett. 9 2007 3401 3404
45. T. Ohmura, Y. Takasaki, H. Furukawa, and M. Suginome Angew. Chem., Int. Ed. 48 2009 2372 2375
46. K. Burgess, and L.D. Jennings J. Am. Chem. Soc. 112 1990 7434 7436
47. S. Bellemin-Laponnaz, J. Tweddell, J.C. Ruble, F.M. Breitling, and G.C. Fu Chem. Commun. 2000 1009 1010
48. E. Vedejs, and J.A. Mackay Org. Lett. 3 2001 535 536
49. S. Yamada, T. Misono, Y. Iwai, A. Masumizu, and Y. Akiyama J. Org. Chem. 71 2006 6872 6880
50. C.Ó. Dálaigh, and S.J. Connon J. Org. Chem. 72 2007 7066 7069
51. X. Li, H. Jiang, E.W. Uffman, L. Guo, Y. Zhang, X. Yang, and V.B. Birman J. Org. Chem. 77 2012 1722 1737
52. B. Hu, M. Meng, S. Jiang, and W. Deng Chin. J. Chem. 30 2012 1289 1294
53. J.L. García Ruano, M.A. Fernández-Ibáñez, J.A. Fernández-Salas, M.C. Maestro, P. Márquez-López, and M.M. Rodríguez-Fernández J. Org. Chem. 74 2009 1200 1204
54. U.E. Campinas, and I. Química Synth. Commun. 33 2003 331 340
55. V. Gembus, J. Bonnet, F. Janin, P. Bohn, V. Levacher, and J. Brière Org. Biomol. Chem. 8 2010 3287 3293
56. I. Shinna, Y. Sano, K. Nakata, M. Suzuki, T. Yokoyama, A. Sasaki, T. Orikasa, T. Miyamoto, M. Ikekita, Y. Nagahara, and Y. Hasome Bioorg. Med. Chem. 15 2007 7599 7617
57. A. Kolleth, M. Cattoen, S. Arseniyadis, and J. Cossy Chem. Commun. 2013 9338 9340
58. A.R. Katritzky, D. Toader, C. Chassaing, and D.C. Aslan J. Org. Chem. 64 1999 6080 6084
59. F. Chen, C.K. Tan, and Y.-Y. Yeung J. Am. Chem. Soc. 135 2013 1232 1235
60. S. Liu, N. Thomson, A. Pettman, Z. Hyder, J. Mo, and J. Xiao J. Mol. Catal. A: Chem. 279 2008 210 217