Kinetic resolution of secondary alcohols using amidine-based catalysts

Journal of Organic Chemistry

Volumn 77, Issue 4, 2012, Pages 1722-1737

  Li, Ximin ^a   Jiang, Hui ^a   Uffman, Eric W ^a   Guo, Lei ^a   Zhang, Yuhua ^a   Yang, Xing ^a   Birman, Vladimir B ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL TRANSFER; ALTERNATIVE METHODS; BENZYLIC; ENANTIOSELECTIVE; ENANTIOSELECTIVE ESTERIFICATION; ESTER HYDROLYSIS; HIGH EFFICACY; KINETIC RESOLUTION; NON-ENZYMATIC; RACEMIC ALCOHOLS; SECONDARY ALCOHOLS;

ESTERS; KINETICS;

CATALYSTS;

ACYLTRANSFERASE; ALCOHOL DERIVATIVE; ALLYL ALCOHOL; AMIDINE; BENZYL ALCOHOL; CYCLOALKANOL DERIVATIVE; PROPARGYLIC ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; KINETIC RESOLUTION; KINETICS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ALKYNES; AMIDINES; BENZYL ALCOHOL; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOPARAFFINS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROPANOLS; STEREOISOMERISM;

EID: 84863116284     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202220x     Document Type: Article

References (113)

1. Cho, B. T. Chem. Soc. Rev. 2009, 38, 443
2. Cho, B. T. Tetrahedron 2006, 62, 7621
3. Wang, C.; Wu, X.; Xiao, J. Chem. Asian J. 2008, 3, 1750
4. Sandoval, C. A.; Ohkuma, T.; Muniz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490
5. Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757
6. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421
7. Pineschi, M. Eur. J. Org. Chem. 2006, 22, 4979
8. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249
9. Williams, J. M. J.; Parker, R. J.; Neri, C. Enzymatic Kinetic Resolution. In Enzyme Catalysis in Organic Synthesis, 2 nd ed.; Drauz, K.; Waldmann, H., Eds.; Wiley-VCH: New York, 2002; Vol. 1, pp 287-312.
10. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974
11. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560
12. Spivey, A. C.; Arseniyadis, S. Top. Curr. Chem. 2010, 291, 233
13. Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012
14. Pellissier, H. Adv. Synth.Catal. 2011, 353, 1613
15. Fu, G. C. Acc. Chem. Res. 2004, 37, 542
16. Kawabata, T.; Yamamoto, K.; Momose, Y.; Yoshida, H.; Nagaoka, Y.; Fuji, K. Chem. Commun. 2001, 2700
17. Spivey, A. C.; Zhu, F.; Mitchell, M. B.; Davey, S. G.; Jarvest, R. L. J. Org. Chem. 2003, 68, 7379
18. Naraku, G.; Shimomoto, N.; Hanamoto, T.; Inanaga, J. Enantiomer 2000, 5, 135
19. Priem, B.; Pelotier, B.; Macdonald, S. J. F.; Anson, M. S.; Campbell, I. B. J. Org. Chem. 2003, 68, 3844
20. Jeong, K.-S.; Kim, S.-H.; Park, H.-J.; Chang, K.-J.; Kim, K. S. Chem. Lett. 2002, 1114
21. Yamada, S.; Misono, T.; Iwai, Y.; Masumizu, A.; Akiyama, Y. J. Org. Chem. 2006, 71, 6872
22. O'Dálaigh, C.; Connon, S. J. J. Org. Chem. 2007, 72, 7066
23. Crittall, M. R.; Rzepa, H. S.; Carbery, D. R. Org. Lett. 2011, 13, 1250
24. Miller, S. J. Acc. Chem. Res. 2004, 37, 601
25. Ishihara, K.; Sakakura, A.; Hatano, M. Synlett 2007, 686
26. Geng, X.-L.; Wang, J.; Li, G.-X.; Chen, P.; Tian, S.-F.; Qu, J. J. Org. Chem. 2008, 73, 8558
27. Hrdina, R.; Muller, C. E.; Schreiner, P. R. Chem. Commun. 2010, 46, 2689
28. Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 2003, 125, 4166
29. Mizuta, S.; Ohtsubo, Y.; Tsuzuki, T.; Fujimoto, T.; Yamamoto, I. Tetrahedron Lett. 2006, 47, 8227
30. Oriyama, T.; Taguchi, H.; Terakado, D.; Sano, T. Chem. Lett. 2002, 26
31. Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347
32. Mitsuda, M.; Tanaka, T.; Tanaka, T.; Demizu, Y.; Onomura, O.; Matsumura, Y. Tetrahedron Lett. 2006, 47, 8073
33. Gissibl, A.; Finn, M. G.; Reiser, O. Org. Lett. 2005, 7, 2325
34. Mazet, C.; Roseblade, S.; Köhler, V.; Pfaltz, A. Org. Lett. 2006, 8, 1879
35. Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226
36. Birman, V. B.; Jiang, H. Org. Lett. 2005, 7, 3445
37. Birman, V. B.; Li, X.; Jiang, H.; Uffman, E. W. Tetrahedron 2006, 62, 285
38. Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351
39. Birman, V. B.; Guo, L. Org. Lett. 2006, 8, 4859
40. Birman, V. B.; Li, X.; Han, Z. Org. Lett. 2007, 9, 37
41. Birman, V. B.; Jiang, H.; Li, X. Org. Lett. 2007, 9, 3237
42. Birman, V. B.; Li, X. Org. Lett. 2008, 10, 1115
43. Li, X.; Liu, P.; Houk, K. N.; Birman, V. B. J. Am. Chem. Soc. 2008, 130, 13836
44. Zhang, Y.; Birman, V. B. Adv. Synth. Catal. 2009, 351, 2525
45. Shiina, I.; Nakata, K. Tetrahedron Lett. 2007, 48, 8314
46. Shiina, I.; Nakata, K.; Ono, K.; Sugimoto, M.; Sekiguchi, A. Chem.-Eur. J. 2010, 16, 167
47. Shiina, I.; Ono, K.; Nakata, K. Chem. Lett. 2011, 40, 147
48. Zhou, H.; Xu, Q.; Chen, P. Tetrahedron 2008, 64, 6494
49. Xu, Q.; Zhou, H.; Geng, X.; Chen, P. Tetrahedron 2009, 65, 2232
50. Chen, P.; Zhang, Y.; Zhou, H.; Xu, Q. Acta Chim. Sin. 2010, 68, 1431
51. Belmessieri, D.; Joannesse, C.; Woods, P. A.; MacGregor, C.; Jones, C.; Campbell, C. D.; Johnston, C. P.; Duguet, N.; Concellon, C.; Bragg, R. A.; Smith, A. D. Org. Biomol. Chem. 2011, 9, 559
52. Kobayashi, M.; Okamoto, S. Tetrahedron Lett. 2006, 47, 4347
53. Hu, B.; Meng, M.; Wang, Z.; Du, W. T.; Fossey, J. S.; Hu, X. Q.; Deng, W. P. J. Am. Chem. Soc. 2010, 132, 17041
54. Hu, B.; Meng, M.; Fossey, J. S.; Mo, W. M.; Hu, X. Q.; Deng, W. P. Chem. Commun. 2011, 47, 10632
55. Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. J. Am. Chem. Soc. 2006, 128, 6536
56. Yang, X.; Bumbu, V. D.; Birman, V. B. Org. Lett. 2011, 13, 4755
57. Purohit, V. C.; Matla, A. S.; Romo, D. J. Am. Chem. Soc. 2008, 130, 10478
58. Leverett, C. A.; Purohit, V. C.; Romo, D. Angew. Chem., Int. Ed. 2010, 49, 9479
59. Belmessieri, D.; Morrill, L. C.; Simal, C.; Slawin, A. M. Z.; Smith, A. D. J. Am. Chem. Soc. 2011, 133, 2714
60. Dietz, F. R.; Gröger, H. Synlett 2008, 663
61. Dietz, F. R.; Gröger, H. Synthesis 2009, 4208
62. Joannesse, C.; Simal, C.; Concellon, C.; Thomson, J. E.; Campbell, C. D.; Slawin, A. M. Z.; Smith, A. D. Org. Biomol. Chem. 2008, 6, 2900
63. Joannesse, C.; Johnston, C. P.; Concellon, C.; Simal, C.; Philp, D.; Smith, A. D. Angew. Chem., Int. Ed. 2009, 48, 8914
64. Shiina, I.; Nakata, K.; Onda, Y. Eur. J. Org. Chem. 2008, 5887
65. Shiina, I.; Nakata, K.; Ono, K.; Onda, Y.; Itagaki, M. J. Am. Chem. Soc. 2010, 132, 11629
66. Yang, X.; Birman, V. B. Adv. Synth. Catal. 2009, 351, 2301
67. Yang, X.; Lu, G.; Birman, V. B. Org. Lett. 2010, 12, 892
68. Yang, X.; Birman, V. B. Angew. Chem., Int. Ed. 2011, 50, 553
69. Yang, X.; Birman, V. B. Chem.-Eur. J. 2011, 17, 11296
70. Bumbu, V. D.; Birman, V. B. J. Am. Chem. Soc. 2011, 133, 13902
71. Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 3268
72. Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2011, 133, 16001
73. Sheppard, C. I.; Taylor, J. L.; Wiskur, S. L. Org. Lett. 2011, 13, 3794
74. Wang, M.; Wang, Z.; Shi, Y.-H.; Shi, X.-X.; Fossey, J. S.; Deng, W.-P. Angew. Chem., Int. Ed. 2011, 50, 4897
75. Shi, Y. H.; Wang, Z.; Hu, B.; Wang, M.; Fossey, J. S.; Deng, W. P. Org. Lett. 2011, 13, 6010
76. Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794
77. Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813
78. Spivey, A. C.; Fekner, T.; Spey, S. E. J. Org. Chem. 2000, 65, 3154 and ref 5i
79. Enantiomeric enrichment of nonracemic 26 using BTM-catalyzed KR has been reported recently: Ball, J. C.; Brennan, P.; Elsunaki, T. M.; Jaunet, A.; Jones, S. Tetrahedron: Asymmetry 2011, 22, 253
80. Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384
81. Nonenzymatic KR of this class of alcohols can be accomplished with high enantioselectivity via asymmetric epoxidation: Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237
82. Bellemin-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009
83. Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535
84. Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091
85. Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265
86. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496
87. Jeong, K. S.; Kim, S. H.; Park, H. J.; Chang, K. J.; Kim, K. S. Chem. Lett. 2002, 1114
88. Dalaigh, C. O.; Hynes, S. J.; O'Brien, J. E.; McCabe, T.; Maher, D. J.; Watson, G. W.; Connon, S. J. Org. Biomol. Chem. 2006, 4, 2785
89. Kawamata, Y.; Oriyama, T. Chem. Lett. 2010, 39, 382
90. References 5k and 34a,34b.
91. Janssen, A. J. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1991, 47, 7645
92. Matharu, D. S.; Morris, D. J.; Clarkson, G. J.; Wills, M. Chem. Commun. 2006, 3232
93. Evans, D. A.; Anderson, J. C.; Taylor, M. K. Tetrahedron Lett. 1993, 34, 5563
94. Hatzakis, N. S.; Smonou, I. Bioorg. Chem. 2005, 33, 325
95. Kantam, M. L.; Yadav, J.; Laha, S.; Srinivas, P.; Sreedhar, B.; Figueras, F. J. Org. Chem. 2009, 74, 4608
96. Ramachandran, P. V.; Gong, B.; Brown, H. C. Tetrahedron Lett. 1994, 35, 2141
97. Fronza, G.; Fuganti, C.; Grasselli, P.; Mele, A. J. Org. Chem. 1991, 56, 6019
98. Silvestri, R.; Artico, M.; Regina, G. L.; Pasquali, A. D.; Martino, G. D.; D'Auria, F. D.; Nencioni, L.; Palamara, A. T. J. Med. Chem. 2004, 49, 3924
99. Solladie-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic, V. Eur. J. Org. Chem. 2000, 6, 1077
100. Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21, 2213
101. Angoli, M.; Barilli, A.; Lesma, G.; Passarella, D.; Riva, S.; Silvani, A.; Danieli, B. J. Org. Chem. 2003, 68, 9525
102. Seemayer, R.; Schneider, M. P. Tetrahedron: Asymmetry 1992, 3, 827
103. Morris, D. J.; Hayes, A. M.; Wills, M. J. Org. Chem. 2006, 71, 7035
104. Martelli, J.; Grée, D.; Kessabi, J.; Grée, R.; Toupet, L. Tetrahedron 1989, 45, 4213
105. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543
106. Akai, S.; Hanada, R.; Fujiwara, N.; Kita, Y.; Egi, M. Org. Lett. 2010, 12, 4900
107. Li, D. R.; He, A.; Falck, J. R. Org. Lett. 2010, 12, 1756
108. Blackmond, D. G.; Hodnett, N. S.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 2006, 128, 7450
109. Adam, W.; Humpf, H.-U.; Roschmann, K. J.; Saha-Möller, C. R. J. Org. Chem. 2001, 66, 5796
110. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129
111. Kawanami, Y.; Mikami, Y.; Hoshino, K.; Suzue, M.; Kajihara, I. Chem. Lett. 2009, 38, 722
112. Stanetty, P.; Mihovilovic, M. D.; Mereiter, K.; Völlenkle, H. Tetrahedron 1998, 54, 875
113. Kashoulis, A.; Gilbert, A.; Ellis-Davies, G. Tetrahedron Lett. 1984, 25, 2905