A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions

Tetrahedron

Volumn 70, Issue 27-28, 2014, Pages 4165-4180

  White, David E ^a   Tadross, Pamela M ^a   Lu, Zhe ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Desymmetrization; Epoxides; Kinetic resolution; Ring opening; Salen

Indexed keywords

ALCOHOL DERIVATIVE; CARBAMIC ACID DERIVATIVE; EPOXIDE; MONOMER; PHENOL DERIVATIVE; WATER;

ARTICLE; CATALYST; CHEMICAL REACTION; DESYMMETRIZATION; ENANTIOSELECTIVITY; NUCLEOPHILICITY; OLIGOMERIZATION; PRIORITY JOURNAL; RING OPENING; SOLUBILITY;

EID: 84901337908     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.03.043     Document Type: Article

References (150)

1. J.F. Larrow, and E.N. Jacobsen Top. Organomet. Chem. 6 2004 123 152
2. M. Tokunaga, J.F. Larrow, F. Kakiuchi, and E.N. Jacobsen Science 277 1997 936 938
3. E.N. Jacobsen Acc. Chem. Res. 33 2000 421 431
4. S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunaga, K.B. Hansen, A.E. Gould, M.E. Furrow, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 1307 1315
5. For reviews of applications of the HKR reaction in industrial and natural products synthesis, see: (a) J.F. Larrow, K.E. Hemberger, S. Jasmin, H. Kabir, and P. Morel Tetrahedron: Asymmetry 14 2003 3589 3592
6. C. Schneider Synthesis 2006 3919 3944
7. P. Kumar, V. Naidu, and P. Gupta Tetrahedron 63 2007 2745 2785
8. Y. Furukawa, T. Suzuki, M. Mikami, K. Kitaori, and H. Yoshimoto J. Synth. Org. Chem. Jpn. 65 2007 308 319
9. P. Kumar, and P. Gupta Synlett 2009 1367 1382
10. H. Pellissier Adv. Synth. Catal. 353 2011 1613 1666
11. For other examples of hydrolytic kinetic resolutions of terminal epoxides, see: (a) J. Chengjun Kinet. Catal. 52 2011 691 696
12. J. Park, K. Lang, K.A. Abboud, and S. Hong Chem. - Eur. J. 17 2011 2236 2245
13. C.J. Jiang, and Z.R. Chen Kinet. Catal. 49 2008 474 478
14. R.B. Kawthekar, and G.-J. Kim Synth. Commun. 38 2008 1236 1248
15. S.S. Thakur, S.-W. Chen, W. Li, C.-K. Shin, Y.-M. Koo, and G.-J. Kim Synth. Commun. 36 2006 2371 2383
16. S.S. Thakur, W. Li, C.-K. Shin, and G.-J. Kim Catal. Lett. 104 2005 151 156
17. S.S. Thakur, W. Li, S.-J. Kim, and G.-J. Kim Tetrahedron Lett. 46 2005 2263 2266
18. C.-K. Shin, S.-J. Kim, and G.-J. Kim Tetrahedron Lett. 45 2004 7429 7433
19. M. Cavazzini, S. Quici, and G. Pozzi Tetrahedron 58 2002 3943 3949
20. S.S. Thakur, W. Li, S.-J. Kim, and G.-J. Kim Stud. Surf. Sci. Catal. 159 2006 205 208
21. S.S. Thakur, W.-J. Li, C.-K. Shin, and G.-J. Kim Chirality 18 2006 37 43
22. S.S. Thakur, S.-W. Chen, W. Li, C.-K. Shin, S.-J. Kin, Y.-M. Koo, and G.-J. Kim J. Organomet. Chem. 691 2006 1862 1872
23. S. Jain, K. Venkatasubbaiah, C.W. Jones, and R.J. Davis J. Mol. Catal. A.: Chem. 316 2010 8 15
24. A. Berkessel, and E. Ertürk Adv. Synth. Catal. 348 2006 2619 2625
25. E.W. Dijk, B.L. Feringa, and G. Roelfes Tetrahedron: Asymmetry 19 2008 2374 2377
26. For reviews on the enzymatic hydrolysis of epoxides, see: (a) M. Schober, and K. Faber Trends Biotechnol. 31 2013 468 478
27. H. Lin, J.-Y. Liu, H.-B. Wang, A.A.Q. Ahmed, and Z.-L. Wu J. Mol. Catal. B: Enzym. 72 2011 77 89
28. N. Bala, and S.S. Chimni Tetrahedron: Asymmetry 21 2010 2879 2898
29. W.J. Choi Appl. Microbiol. Biotechnol. 84 2009 239 247
30. M.S. Smit, and M. Labuschagne Curr. Org. Chem. 10 2006 1145 1161
31. W.J. Choi, and C.Y. Choi Biotechnol. Bioprocess Eng. 10 2005 167 179
32. M.S. Smit Trends Biotechnol. 22 2004 123 129
33. E.J. de Vries, and D.B. Janssen Curr. Opin. Biotechnol. 14 2003 414 420
34. A. Steinreiber, and K. Faber Curr. Opin. Biotechnol. 12 2001 552 558
35. A. Archelas, and R. Furstoss Curr. Opin. Chem. Biol. 5 2001 112 119
36. S.C. Sinha, E. Keinan, and J.-L. Reymond J. Am. Chem. Soc. 115 1993 4893 4894
37. J.M. Ready, and E.N. Jacobsen J. Am. Chem. Soc. 121 1999 6086 6087
38. G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, P. Melchiorre, and L. Sambri Org. Lett. 6 2004 3973 3975
39. G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, P. Melchiorre, and L. Sambri Org. Lett. 7 2005 1983 1985
40. For other approaches to the phenolytic kinetic resolution of terminal epoxides, see: (a) T. Aral, M. Karakaplan, and H. Hosgören Catal. Lett. 142 2012 794 802
41. R.B. Kawthekar, Y.-H. Lee, and G.-J. Kim J. Porous Mater. 16 2009 367 378
42. Y.-S. Kim, X.-F. Guo, and G.-J. Kim Top. Catal. 52 2009 197 204
43. K.-Y. Lee, Y.-H. Lee, C.-K. Shin, and G.-J. Kim Stud. Surf. Sci. Catal. 165 2007 467 470
44. K.-Y. Lee, C.-Y. Lee, and G.-J. Kim React. Kinet. Catal. Lett. 93 2008 75 83
45. R.B. Kawthekar, C.-H. Ahn, and G.-J. Kim Catal. Lett. 115 2007 62 69
46. W. Solodenko, G. Jas, U. Kunz, and A. Kirschning Synthesis 2007 583 589
47. L. Karadeniz, G. Koz, K. Aydin, and S.T. Astley Turk. J. Chem. 34 2010 711 718
48. For additional examples of the aminolytic kinetic resolution of terminal and internal epoxides, see: (a) H. Bao, Z. Wang, T. You, and K. Ding Chin. J. Chem. 31 2013 67 71
49. B. Plancq, and T. Ollevier Chem. Commun. 2012 3806 3808
50. X. Hu, B. Gao, Y. Chu, W. Li, X. Liu, L. Lin, and X. Feng Chem. - Eur. J. 18 2012 3473 3477
51. K. Arai, S. Lucarini, M.M. Salter, K. Ohta, Y. Yamashita, and S. Kobayashi J. Am. Chem. Soc. 129 2007 8103 8111
52. K. Arai, M.M. Salter, Y. Yamashita, and S. Kobayashi Angew. Chem., Int. Ed. 46 2007 955 957
53. R.I. Kureshy, M. Kumar, S. Agrawal, N.H. Khan, S.H.R. Abdi, and H.C. Bajaj Tetrahedron: Asymmetry 21 2010 451 456
54. G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, M. Massaccesi, P. Melchiorre, and L. Sambri Org. Lett. 6 2004 2173 2176
55. Intramolecular additions of alcohols to terminal and meso epoxides could be effected with good enantioselectivity using monomer 1: M.H. Wu, K.B. Hansen, and E.N. Jacobsen Angew. Chem., Int. Ed. 38 1999 2012 2014
56. The desymmetrization of meso epoxides with benzoic acid as nucleophile is catalyzed with moderate-to-high enantioselectivity using monomer 1: E.N. Jacobsen, F. Kakiuchi, R.G. Konsler, J.F. Larrow, and M. Tokunaga Tetrahedron Lett. 38 1997 773 776
57. For a discussion of practical considerations in the HKR and other kinetic resolution processes, see: J.M. Keith, J.F. Larrow, and E.N. Jacobsen Adv. Synth. Catal. 343 2001 5 26
58. L.P.C. Nielsen, C.P. Stevenson, D.G. Blackmond, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 1360 1362
59. L.P.C. Nielsen, S.J. Zuend, D.D. Ford, and E.N. Jacobsen J. Org. Chem. 77 2012 2486 2495
60. 3: K.B. Hansen, J.L. Leighton, and E.N. Jacobsen J. Am. Chem. Soc. 118 1996 10924 10925 Also see Ref. 2b
61. The transition structure representation in Fig. 1 is based on detailed experimental and computational analyses reported in: D.D. Ford, L.P.C. Nielsen, S.J. Zuend, C.B. Musgrave, and E.N. Jacobsen J. Am. Chem. Soc. 135 2013 15595 15608
62. For reviews, see Ref. 1 and:(a) N. Madhavan, C.W. Jones, and M. Weck Acc. Chem. Res. 41 2008 1153 1165
63. R.M. Haak, S.J. Wezenberg, and A.W. Kleij Chem. Commun. 2010 2713 2723
64. S. Matsunaga, and M. Shibasaki Synthesis 2013 421 437
65. R.G. Konsler, J. Karl, and E.N. Jacobsen J. Am. Chem. Soc. 120 1998 10780 10781
66. S. Peukert, and E.N. Jacobsen Org. Lett. 1 1999 1245 1248
67. D.A. Annis, and E.N. Jacobsen J. Am. Chem. Soc. 121 1999 4147 4154
68. R. Breinbauer, and E.N. Jacobsen Angew. Chem., Int. Ed. 39 2000 3604 3607
69. T. Belser, and E.N. Jacobsen Adv. Synth. Catal. 350 2008 967 971
70. 1 symmetric salen units, see Ref. 17 and (a) A.W. Kleij Eur. J. Inorg. Chem. 2009 193 205
71. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S.T. Patel, and R.V. Jasra J. Mol. Catal. A: Chem. 179 2002 73 77
72. Y. Song, H. Chen, X. Hu, C. Bai, and Z. Zheng Tetrahedron Lett. 44 2003 7081 7085
73. R.I. Kureshy, S. Singh, N.H. Khan, S.H.R. Abdi, I. Ahmad, A. Bhatt, and R.V. Jasra Chirality 17 2005 590 594
74. M. Holbach, and M. Weck J. Org. Chem. 71 2006 1825 1836
75. X. Zheng, C.W. Jones, and M. Weck Chem. - Eur. J. 12 2006 576 583
76. B.M. Rossbach, K. Leopold, and R. Weberskirch Angew. Chem., Int. Ed. 45 2006 1309 1312
77. W. Solodenko, G. Jas, U. Kunz, and A. Kirschning Synthesis 2007 583 589
78. X. Zheng, C.W. Jones, and M. Weck J. Am. Chem. Soc. 129 2007 1105 1112
79. R.I. Kureshy, K.J. Prathap, S. Singh, S. Agrawal, N.H. Khan, S.H.R. Abdi, and R.V. Jasra Chirality 19 2007 809 815
80. C.S. Gill, K. Venkatasubbaiah, N.T.S. Phan, M. Weck, and C.W. Jones Chem. - Eur. J. 14 2008 7306 7313
81. P. Goyal, X. Zheng, and M. Weck Adv. Synth. Catal. 350 2008 1816 1822
82. M. Beigi, S. Roller, R. Haag, and A. Liese Eur. J. Org. Chem. 2008 2135 2141
83. C.S. Gill, W. Long, and C.W. Jones Catal. Lett. 131 2009 425 431
84. X. Zhu, K. Venkatasubbaiah, M. Weck, and C.W. Jones J. Mol. Catal. A: Chem. 329 2010 1 6
85. R.M. Thomas, P.C.B. Widger, S.M. Ahmed, R.C. Jeske, W. Hirahata, E.B. Lobkovsky, and G.W. Coates J. Am. Chem. Soc. 132 2010 16520 16525
86. S.J. Wezenberg, and A.W. Kleij Adv. Synth. Catal. 352 2010 85 91
87. Y. Liu, J. Rawlston, A.T. Swann, T. Takatani, C.D. Sherrill, P.J. Ludovice, and M. Weck Chem. Sci. 2 2011 429 438
88. M.G.C. Kahn, and M. Weck Catal. Sci. Technol. 2 2012 386 389
89. M.G.C. Kahn, J.H. Stenlid, and M. Weck Adv. Synth. Catal. 354 2012 3016 3024
90. C. Zhu, G. Yuan, X. Chen, Z. Yang, and Y. Cui J. Am. Chem. Soc. 134 2012 8058 8061
91. D.-Y. Ma, Z.-Y. Xiao, J. Etxabe, and K. Warnmark ChemCatChem 4 2012 1321 1329
92. K. Matkiewicz, A. Bukowska, and W. Bukowski J. Mol. Catal. A: Chem. 368-369 2013 43 52
93. K. Venkatasubbaiah, Y. Feng, T. Arrowood, P. Nickias, and C.W. Jones ChemCatChem 5 2013 201 209
94. S.M. Ahmed, A. Poater, M.I. Childers, P.C.B. Widger, A.M. LaPointe, E.B. Lobkovsky, G.W. Coates, and L. Cavallo J. Am. Chem. Soc. 135 2013 18901 18911
95. J.M. Ready, and E.N. Jacobsen J. Am. Chem. Soc. 123 2001 2687 2688
96. J.M. Ready, and E.N. Jacobsen Angew. Chem., Int. Ed. 41 2002 1374 1377
97. 2 symmetric salen units, see: (a) Y. Song, X. Yao, H. Chen, C. Bai, X. Hu, and Z. Zheng Tetrahedron Lett. 43 2002 6625 6627
98. M.-A. Kwon, and G.-J. Kim Catal. Today 87 2003 145 151
99. N.C. Gianneschi, P.A. Bertin, S.T. Nguyen, C.A. Mirkin, L.N. Zakharov, and A.L. Rheingold J. Am. Chem. Soc. 125 2003 10508 10509
100. N.C. Gianneschi, S.-H. Cho, S.T. Nguyen, and C.A. Mirkin Angew. Chem., Int. Ed. 43 2004 5503 5507
101. L.L. Welbes, R.C. Scarrow, and A.S. Borovik Chem. Commun. 2004 2544 2545
102. R.I. Kureshy, S. Singh, N.H. Khan, S.H.R. Abdi, S. Agrawal, and R.V. Jasra Tetrahedron: Asymmetry 17 2006 1638 1643
103. R.M. Haak, M.M. Belmonte, E.C. Escudero-Adan, J. Benet-Buchholz, and A.W. Kleij Dalton Trans. 39 2010 593 602
104. A. Zulauf, M. Mellah, and E. Schulz Chem. - Eur. J. 16 2010 11108 11114
105. R.I. Kureshy, K.J. Prathap, M. Kumar, P.K. Bera, N.H. Khan, S.H.R. Abdi, and H.C. Bajaj Tetrahedron 67 2011 8300 8307
106. A. Sadhukhan, N.H. Khan, T. Roy, R.I. Kureshy, S.H.R. Abdi, and H.C. Bajaj Chem. - Eur. J. 18 2012 5256 5260
107. X. Hong, M. Mellah, F. Bordier, R. Guillot, and E. Schulz ChemCatChem 4 2012 1115 1121
108. M. Kumar, R.I. Kureshy, A.K. Shah, A. Das, N.H. Khan, S.H.R. Abdi, and H.C. Bajaj J. Org. Chem. 78 2013 9076 9084
109. X. Hong, L. Billon, M. Mellah, and E. Schulz Catal. Sci. Technol. 3 2013 723 729
110. D.E. White, and E.N. Jacobsen Tetrahedron: Asymmetry 14 2003 3633 3638
111. Selected examples of the application of 4a in the synthesis of complex targets: (a) A. Peloruside, M.A. McGowan, C.P. Stevenson, M.A. Schiffler, and E.N. Jacobsen Angew. Chem., Int. Ed. 49 2010 6147 6150
112. Sch 642305: B.B. Snider, and J. Zhou Org. Lett. 8 2006 1283 1286
113. A. Moenomycin, M. Adachi, Y. Zhang, C. Leimkuhler, B. Sun, J.V. LaTour, and D.E. Kahne J. Am. Chem. Soc. 128 2006 14012 14013
114. Hexose derivatives: D.J. Covell, N.A. Vermeulen, N.A. Labenz, and M.C. White Angew. Chem., Int. Ed. 45 2006 8217 8220
115. Indolodioxane U86192A: J. Chae, and S.L. Buchwald J. Org. Chem. 69 2004 3336 3339
116. Reserpine: N.S. Rajapaksa, M.A. McGowan, M. Rienzo, and E.N. Jacobsen Org. Lett. 15 2013 706 709
117. R.N. Loy, and E.N. Jacobsen J. Am. Chem. Soc. 131 2009 2786 2787
118. J.A. Birrell, and E.N. Jacobsen Org. Lett. 15 2013 2895 2897
119. An unoptimized version of the first two steps of this procedure has been reported: P. Vachal, and E.N. Jacobsen Org. Lett. 2 2000 867 870
120. A. Samat, M.E.M. Bibout, and J. Elguéro Heterocycles 19 1982 469 472
121. In the case of methyl glycidate, considerable foaming hampered distillation of the product mixture on the laboratory scale. However, removal of the diol product by aqueous extraction prior to distillation circumvented the foaming problem, and the epoxide was thus isolated in good yield: C.P. Stevenson, L.P.C. Nielsen, and E.N. Jacobsen Org. Synth. 83 2006 162 169
122. With monomer 1b·2,6-lutidine, the resolution of styrene oxide with phenol provided a 3:2 ratio of the undesired internal addition product to the desired α-aryloxy alcohol: J.M. Ready Ph.D. Thesis 2001 Harvard University Cambridge, MA
123. For example, see: D.M. Dishong, C.J. Diamond, M.I. Cinoman, and G.W. Gokel J. Am. Chem. Soc. 105 1983 586 593
124. For examples of phenolytic desymmetrization of meso epoxides, see: (a) T. Iida, N. Yamamoto, S. Matsunaga, H.-G. Woo, and M. Shibasaki Angew. Chem., Int. Ed. 37 1998 2223 2226
125. E.M. Vogl, S. Matsunaga, M. Kanai, T. Iida, and M. Shibasaki Tetrahedron Lett. 39 1998 7917 7920
126. S. Matsunaga, J. Das, J. Roels, E.M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, and M. Shibasaki J. Am. Chem. Soc. 122 2000 2252 2260
127. S. Matsunaga, T. Ohshima, and M. Shibasaki Adv. Synth. Catal. 344 2002 3 15 For examples of the alcoholytic desymmetrization of meso epoxides, see
128. C. Schneider, A.R. Skreekanth, and E. Mai Angew. Chem., Int. Ed. 43 2004 5691 5694
129. A. Tschöp, A. Marx, A.R. Sreekanth, and C. Schneider Eur. J. Org. Chem. 2007 2318 2327 For the catalytic asymmetric co-polymerization of carbon dioxide and meso epoxides to form polycarbonates, see
130. K. Nozaki, K. Nakano, and T. Hiyama J. Am. Chem. Soc. 121 1999 11008 11009
131. M. Cheng, N.A. Darling, E.B. Lobkovsky, and G.W. Coates Chem. Commun. 2000 2007 2008
132. For examples of enzymatic hydrolytic desymmetrization of meso epoxides, see: (a) L. Zhao, B. Han, Z. Huang, M. Miller, H. Huang, D.S. Malashock, Z. Zhu, A. Milan, D.E. Robertson, D.P. Weiner, and M.J. Burk J. Am. Chem. Soc. 126 2004 11156 11157 and references therein
133. C.A.G.M. Weijers Tetrahedron: Asymmetry 8 1997 639 647
134. D.M. Hodgson, A.R. Gibbs, and G.P. Lee Tetrahedron 52 1996 14361 14384 and references therein
135. K.L. Servis, and E.A. Noe J. Am. Chem. Soc. 95 1973 171 174 and references therein
136. For examples of the carbamolytic desymmetrization of meso epoxides, see:(a) A. Sekine, T. Ohshima, and M. Shibasaki Tetrahedron 58 2002 75 82
137. X.-L. Hou, J. Wu, L.-X. Dai, L.-J. Xia, and M.-H. Tang Tetrahedron: Asymmetry 9 1998 1747 1752
138. X.-L. Fu, and S.-H. Wu Synth. Commun. 27 1997 1677 1683
139. S. Regati, Y. He, M. Thimmaiah, P. Li, S. Xiang, B. Chen, and J.C.-G. Zhao Chem. Commun. 2013 9836 9838
140. S. Azoulay, K. Manabe, and S. Kobayashi Org. Lett. 7 2005 4593 4595
141. E. Mai, and C. Schneider Synlett 2007 2136 2138
142. F. Carrée, R. Gil, and J. Collin Org. Lett. 7 2005 1023 1026
143. S. Chang, D. McNally, S. Shary-Tehrany, M.J. Hickey, and R.H. Boyd J. Am. Chem. Soc. 92 1970 3109 3118
144. N.L. Allinger, M.T. Tribble, M.A. Miller, and D.H. Wertz J. Am. Chem. Soc. 93 1971 1637 1648
145. For examples of the desymmetrization of oxetanes with other nucleophiles, see: (a) Z. Wang, Z. Chen, and J. Sun Angew. Chem., Int. Ed. 52 2013 6685 6688
146. Z. Chen, Z. Wang, and J. Sun Chem. Eur. J. 19 2013 8426 8430
147. M. Mizuno, M. Kanai, A. Iida, and K. Tomioka Tetrahedron: Asymmetry 7 1996 2483 2484
148. M. Mizuono, M. Kanai, A. Iida, and K. Tomioka Tetrahedron 53 1997 10699 10708
149. K.M. Chenault, M.-J. Kim, A. Akiyama, T. Miyazawa, E.S. Simon, and G.W. Whitesides J. Org. Chem. 52 1987 2608 2611
150. A.F. Cunningham Jr., and E.P. Kündig J. Org. Chem. 53 1988 1823 1825