Stereoselective cyclization reactions under phase-transfer catalysis

Tetrahedron

Volumn 70, Issue 11, 2014, Pages 1935-1960

  Herchl, Richard ^a   Waser, Mario ^a  

^a JOHANNES KEPLER UNIVERSITY LINZ   (Austria)

Author keywords

Asymmetric phase transfer catalysis; Cyclization reactions; Organocatalysis; Stereoselective catalysis

Indexed keywords

CARBON; CYCLOPENTANE DERIVATIVE; FLAVANONE DERIVATIVE; NITROGEN; OXAZOLIDINE DERIVATIVE; PYRAZOLIDINE DERIVATIVE; PYRAZOLINE DERIVATIVE; SINGLE HETEROCYCLIC RINGS; TETRAHYDROFURAN DERIVATIVE; TRIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; AZIRIDINE DERIVATIVE; CHALCONE; PYRAZOLE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; AZIRIDINATION; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CLAISEN CONDENSATION; CYCLIZATION; CYCLOPROPANATION; DARZENS REACTION; DIASTEREOISOMER; DIAZIRIDINATION; ENANTIOSELECTIVITY; EPOXIDATION; PHASE TRANSFER CATALYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; ONE POT SYNTHESIS;

EID: 84896703999     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.01.050     Document Type: Review

References (155)

1. H.N.C. Wong, X.-L. Hou, K.-S. Yeung, and H. Huang K.C. Majumdar, S.K. Chattopadhyay, Heterocycles in Natural Product Synthesis 2011 Wiley-VCH Weinheim, Germany
2. B. Alcaide, and P. Almendros G.W. Gribble, J.A. Joule, Progress in Heterocyclic Chemistry 2011 Elsevier New York, NY
3. B. Das, and K. Damodar K.C. Majumdar, S.K. Chattopadhyay, Heterocycles in Natural Product Synthesis 2011 Wiley-VCH Weinheim, Germany
4. A. Berkessel, and H. Gröger Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis 2005 Wiley-VCH Weinheim, Germany
5. I. Dalko Enantioselective Organocatalysis 2007 Wiley-VCH Weinheim, Germany
6. J. Seayad, and B. List Org. Biomol. Chem. 3 2005 719 724
7. S. Bertelsen, and K.A. Jørgensen Chem. Soc. Rev. 38 2009 2178 2189
8. A. Dondoni, and A. Massi Angew. Chem., Int. Ed. 47 2008 4638 4660
9. D.W.C. MacMillan Nature 455 2008 304 308
10. M. Waser A.D. Kinghorn, H. Falk, J. Kobayashi, Prog. Chem. Org. Nat. Prod. Vol. 96 2012 Springer
11. E.V. Dehmlow, and S.S. Dehmlow Phase Transfer Catalysis 3rd ed. 1993 Wiley-VCH Weinheim, Germany
12. C.M. Starks, C.L. Liotta, and M. Halpern Phase-transfer Catalysis 1994 Chapman & Hall New York, NY
13. Y. Sasson, and R. Neumann Handbook of Phase-Transfer Catalysis 1997 Blackie Academic & Professional London, UK
14. M.E. Halpern Phase-Transfer Catalysis ACS Symposium Series Vol. 659 1997 American Chemical Society Washington, DC
15. R. Helder, J.C. Hummelen, R.W.P.M. Laane, J.S. Wiering, and H. Wynberg Tetrahedron Lett. 17 1976 1831 1834
16. U.H. Dolling, P. Davis, and E.J.J. Grabowski J. Am. Chem. Soc. 106 1984 446 447
17. T. Shioiri Y. Sasson, R. Neumann, Handbook of Phase-Transfer Catalysis 1997 Blackie Academic & Professional London, UK Chapter 14
18. A. Nelson Angew. Chem., Int. Ed. 38 1999 1583 1585
19. T. Shioiri, and S. Arai F. Vögtle, J.F. Stoddart, M. Shibasaki, Stimulating Concepts in Chemistry 2000 Wiley-VCH Weinheim, Germany 123
20. M.J. O'Donnell I. Ojima, Catalytic Asymmetric Syntheses 2nd ed. 2000 Wiley-VCH New York, NY Chapter 10
21. M.J. O'Donnell Aldrichimica Acta 34 2001 3 15
22. K. Maruoka, and T. Ooi Chem. Rev. 103 2003 3013 3028
23. M.J. O'Donnell Acc. Chem. Res. 37 2004 506 517
24. B. Lygo, and B.I. Andrews Acc. Chem. Res. 37 2004 518 525
25. J. Vachon, and J. Lacour Chimia 60 2006 266 275
26. T. Hashimoto, and K. Maruoka Chem. Rev. 107 2007 5656 5682
27. T. Ooi, and K. Maruoka Angew. Chem., Int. Ed. 46 2007 4222 4266
28. K. Maruoka Org. Process Res. Dev. 12 2008 679 697
29. K. Maruoka Asymmetric Phase Transfer Catalysis 2008 Wiley-VCH Weinheim, Germany
30. S.-S. Jew, and H.G. Park Chem. Commun. 2009 7090 7103
31. K. Maruoka, and S. Shirakawa Angew. Chem., Int. Ed. 52 2013 4312 4348
32. For an illustrative example highlighting the potential of such an approach see: S. Arai, K. Nakayama, Y. Suzuki, K. Hatano, and T. Shioiri Tetrahedron Lett. 39 1998 9739 9742
33. M.J. Porter, and J. Skidmore Chem. Commun. 2000 1215 1225
34. T. Nemoto, T. Ohshima, and M. Shibasaki J. Synth. Org. Chem. Jpn. 60 2002 94 105
35. S. Arai, H. Tsuge, and T. Shioiri Tetrahedron Lett. 39 1998 7563 7566
36. S. Arai, H. Tsuge, M. Oku, M. Miura, and T. Shioiri Tetrahedron 58 2002 1623 1630
37. E.J. Corey, and F.-Y. Zhang Org. Lett. 1 1999 1287 1290
38. B. Lygo, and D.C.M. To Tetrahedron Lett. 42 2001 1343 1346
39. B. Lygo, S.D. Gardiner, M.C. McLeod, and D.C.M. To Org. Biomol. Chem. 5 2007 2283 2290
40. J. Ye, Y. Wang, R. Liu, G. Zhang, Q. Zhang, J. Chen, and X. Liang Chem. Commun. 2003 2714 2715
41. J. Ye, Y. Wang, J. Chen, and X. Liang Adv. Synth. Catal. 346 2004 691 696
42. M.-S. Yoo, D.-G. Kim, M.W. Ha, S.-S. Jew, H.-G. Park, and B.-S. Jeong Tetrahedron Lett. 51 2010 5601 5603
43. K. Hori, M. Tamura, K. Tani, N. Nishiwaki, M. Ariga, and Y. Tohda Tetrahedron Lett. 47 2006 3115 3118
44. A. Makó, Z. Rapi, G. Keglevich, Á. Szöllösy, L. Drahos, L. Hegedüs, and P. Bakó Tetrahedron: Asymmetry 21 2010 919 925
45. S.-S. Jew, J.-H. Lee, B.-S. Jeong, M.-S. Yoo, M.-J. Kim, Y.-J. Lee, J. Lee, S.-H. Choi, K. Lee, M.S. Lah, and H.-G. Park Angew. Chem., Int. Ed. 44 2005 1383 1385
46. J. Lv, X. Wang, J. Liu, L. Zhang, and Y. Wang Tetrahedron: Asymmetry 17 2006 330 335
47. E.V. Dehmlow, S. Düttmann, B. Neumann, and H.-G. Stammler Eur. J. Org. Chem. 2002 2087 2093
48. A. Berkessel, M. Guixà, F. Schmidt, J.M. Neudörfl, and J. Lex Chem. - Eur. J. 13 2007 4483 4498
49. W. Adam, P.B. Rao, H.-G. Degen, and C.R. Saha-Möller Tetrahedron: Asymmetry 12 2001 121 125
50. W. Adam, R.B. Rao, H.-G. Degen, A. Levai, T. Patonay, and C.R. Saha-Möller J. Org. Chem. 67 2002 259 264
51. B. Lygo, and D.C.M. To Chem. Commun. 2002 2360 2361
52. For a review about bifunctional ammonium salt catalysts and further references see: J. Novacek, and M. Waser Eur. J. Org. Chem. 2013 637 648
53. T. Ooi, D. Ohara, M. Tamura, and K. Maruoka J. Am. Chem. Soc. 126 2004 6844 6845
54. R.L. Dorow, and S.A. Tymonko Tetrahedron Lett. 47 2006 2493 2495
55. Y. Wang, J. Ye, and X. Liang Adv. Synth. Catal. 349 2007 1033 1036
56. B. Lygo, S.D. Gardiner, and D.C.M. To Synlett 2006 2063 2066
57. V.K. Aggarwal, C. Lopin, and F. Sandrinelli J. Am. Chem. Soc. 125 2003 7596 7601
58. R. Novikov, G. Bernardinelli, and J. Lacour Adv. Synth. Catal. 351 2009 596 606
59. P.C. Bulman Page, C.J. Bartlett, Y. Chan, D. Day, P. Parker, B.R. Buckley, G.A. Rassias, A.M.Z. Slawin, S.M. Allin, J. Lacour, and A. Pinto J. Org. Chem. 77 2012 6128 6138
60. H. Kawai, S. Okusu, Z. Yuan, E. Tokunaga, A. Yamano, M. Shiro, and N. Shibata Angew. Chem., Int. Ed. 52 2013 2221 2225
61. G. Darzens Comput. Rend. 151 1911 883 884
62. S. Arai, and T. Shioiri Tetrahedron Lett. 39 1998 2145 2148
63. S. Arai, Y. Shirai, T. Ishida, and T. Shioiri Tetrahedron 55 1999 6375 6386
64. S. Arai, Y. Shirai, T. Ishida, and T. Shioiri Chem. Commun. 1999 49 50
65. S. Arai, K. Tokumaru, and T. Aoyama Tetrahedron Lett. 45 2004 1845 1848
66. S. Arai, T. Ishida, and T. Shioiri Tetrahedron Lett. 39 1998 8299 8302
67. S. Arai, and T. Shioiri Tetrahedron 58 2002 1407 1413
68. J.-M. Ku, M.-S. Yoo, H.-G. Park, S.-S. Jew, and B.-S. Jeong Tetrahedron 63 2007 8099 8103
69. Y. Liu, B.A. Provencher, K.J. Bartelson, and L. Deng Chem. Sci. 2 2011 1301 1304
70. P. Bakó, Z. Rapi, G. Keglevich, T. Szabó, P.L. Sóti, T. Vígh, A. Grün, and T. Holczbauer Tetrahedron Lett. 52 2011 1473 1476
71. Z. Rapi, T. Szabó, G. Keglevich, Á. Szöllösy, L. Drahos, and P. Bakó Tetrahedron: Asymmetry 22 2011 1189 1196
72. Z. Rapi, P. Bakó, G. Keglevich, Á. Szöllösy, L. Drahos, A. Botyánszki, and T. Holczbauer Tetrahedron: Asymmetry 23 2012 489 496
73. D. Tanner Angew. Chem., Int. Ed. Engl. 33 1994 599 619
74. W. McCoull, and F.A. Davis Synthesis 2000 1347 1365
75. J. Aires-de-Sousa, A.M. Lobo, and S. Prabhakar Tetrahedron Lett. 37 1996 3183 3186
76. E. Murugan, and A. Siva Synthesis 2005 2022 2028
77. S. Minakata, Y. Murakami, R. Tsuruoka, S. Kitanaka, and M. Komatsu Chem. Commun. 2008 6363 6365
78. Y. Murakami, Y. Takeda, and S. Minakata J. Org. Chem. 76 2011 6277 6285
79. S. Aichhorn, G.N. Gururaja, and M. Waser RSC Adv. 3 2013 4552 4557
80. Herchl, R.; Waser, M. unpublished results.
81. R.G. Kostyanovsky, R. Murugan, and M. Sutharchanadevi A. Padwa, Comprehensive Heterocyclic Chemistry II Vol. 1A 1996 Elsevier Oxford, UK 347
82. G.D. McAllister, A. Perry, and R.J.K. Taylor A. Padwa, Comprehensive Heterocyclic Chemistry III Vol. 1 2008 Elsevier New York, NY 539
83. N.N. Makhova, A.V. Shevtsov, and V.Y. Petukhova Russ. Chem. Rev. 80 2011 1035 1066
84. L. Lykke, K.S. Halskov, B.D. Carlsen, V.X. Chen, and K.A. Jørgensen J. Am. Chem. Soc. 135 2013 4692 4695
85. H.-U. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151 1196
86. J.E. Baldwin Chem. Rev. 103 2003 1197 1212
87. A. Brandi, S. Cicchi, F.M. Cordero, and A. Goti Chem. Rev. 103 2003 1213 1270
88. F.D. Simone, and J. Waser Synthesis 2009 3353 3374
89. D. Zhang, H. Song, and Y. Qin Acc. Chem. Res. 44 2011 447 457
90. J.M. McIntosh, and H. Khalil Can. J. Chem. 56 1978 2134 2138
91. R.K. Singh, and S. Danishefsky J. Org. Chem. 40 1975 2969 2970
92. S.I. Kozhushkov, A. Leonov, and A. de Meijere Synthesis 2003 956 958
93. G.V. Kryshtal, G.M. Zhdankina, and S.G. Zlotin Russ. Chem. Bull., Int. Ed. 60 2011 2286 2290
94. S. Arai, K. Nakayama, T. Ishida, and T. Shioiri Tetrahedron Lett. 40 1999 4215 4218
95. C.D. Fiandra, L. Piras, F. Fini, P. Disetti, M. Moccia, and M.F.A. Adamo Chem. Commun. 2012 3863 3865
96. R. Herchl, and M. Waser Tetrahedron Lett. 54 2013 2472 2475
97. M. Waser, K. Gratzer, R. Herchl, and N. Müller Org. Biomol. Chem. 10 2012 251 254
98. K. Gratzer, and M. Waser Synthesis 44 2012 3661 3670
99. G.N. Gururaja, R. Herchl, A. Pichler, K. Gratzer, and M. Waser Molecules 18 2013 4357 4372
100. K.M. Belyk, B. Xiang, P.G. Bulger, W.R. Leonard Jr., J. Balsells, J. Yin, and C.-Y. Chen Org. Process Res. Dev. 14 2010 692 700
101. T. Kull, and R. Peters Angew. Chem., Int. Ed. 47 2008 5461 5464
102. T. Kull, J. Cabrera, and R. Peters Chem. - Eur. J. 16 2010 9132 9139
103. P. Meier, F. Broghammer, K. Latendorf, G. Rauhut, and R. Peters Molecules 17 2012 7121 7150
104. W.J. Nodes, K. Shankland, S. Rajkumar, and A.J.A. Cobb Synlett 2010 3011 3014
105. V. Gembus, S. Postikova, V. Levacher, and J.-F. Brière J. Org. Chem. 76 2011 4194 4199
106. For a review on saturated heterocycles see: A. Hutchinson, and A. Nadin J. Chem. Soc., Perkin Trans. 1 2000 2862 2892
107. Y.-G. Wang, H. Mii, T. Kano, and K. Maruoka Bioorg. Med. Chem. Lett. 19 2009 3795 3797
108. T. Kano, R. Sakamoto, H. Mii, Y.-G. Wang, and K. Maruoka Tetrahedron 66 2010 4900 4904
109. S. Shirakawa, Y. Liu, A. Usui, and K. Maruoka ChemCatChem 4 2012 980 982
110. Y. Liu, A. Usui, S. Shirakawa, and K. Maruoka Asian J. Org. Chem. 1 2012 180 186
111. B. Lygo, C. Beynon, M.C. McLeod, C.-E. Roy, and C.E. Wade Tetrahedron 66 2010 8832 8836
112. B. Lygo, C. Beynon, C. Lumley, M.C. McLeod, and C.E. Wade Tetrahedron Lett. 50 2009 3363 3365
113. H. Kawai, Y. Sugita, E. Tokunaga, H. Sato, M. Shiro, and N. Shibata Chem. Commun. 2012 3632 3634
114. T. Ooi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 125 2003 5139 5151
115. S.L. Castle, and G.S.C. Srikanth Org. Lett. 5 2003 3611 3614
116. T. Ma, X. Fu, C.W. Kee, L. Zong, Y. Pan, K.-W. Huang, and C.-H. Tan J. Am. Chem. Soc. 133 2011 2828 2831
117. A.E. Sheshenev, E.V. Boltukhina, A.J.P. White, and K.K. Hii Angew. Chem. 125 2013 7126 7129
118. J. Nie, M.-Q. Hua, H.-Y. Xiong, Y. Zheng, and J.-A. Ma J. Org. Chem. 77 2012 4209 4216
119. H. Kawai, Z. Yuan, T. Kitayama, E. Tokunaga, and N. Shibata Angew. Chem., Int. Ed. 52 2013 5575 5579
120. T.A. Moss, D.R. Fenwick, and D.J. Dixon J. Am. Chem. Soc. 130 2008 10076 10077
121. T.A. Moss, D.M. Barber, A.F. Kyle, and D.J. Dixon Chem. - Eur. J. 19 2013 3071 3081
122. E.E. Maciver, S. Thompson, and M.D. Smith Angew. Chem., Int. Ed. 48 2009 9979 9982
123. E.E. Maciver, P.C. Knipe, A.P. Cridland, A.L. Thompson, and M.D. Smith Chem. Sci. 3 2012 537 540
124. M. Li, P.A. Woods, and M.D. Smith Chem. Sci. 4 2013 2907 2911
125. During the evaluation of this manuscript the use of a similar bifunctional PTC for the synthesis of enantioenriched α-amino ester derivatives of 3-substituted phthalides was reported: M. Perillo, A. Di Mola, R. Filosa, L. Palombi, and A. Massa RSC Adv. 4 2014 4239 4246
126. T. Shibuguchi, H. Mihara, A. Kuramochi, S. Sakuraba, T. Ohshima, and M. Shibasaki Angew. Chem., Int. Ed. 45 2006 4635 4637
127. T. Shibuguchi, H. Mihara, A. Kuramochi, T. Ohshima, and M. Shibasaki Chem. - Asian J. 2 2007 794 801
128. Y.-G. Wang, T. Kumano, T. Kano, and K. Maruoka Org. Lett. 11 2009 2027 2029
129. R. He, S. Shirakawa, and K. Maruoka J. Am. Chem. Soc. 131 2009 16620 16621
130. O. Mahé, I. Dez, V. Levacher, and J.-F. Brière Angew. Chem., Int. Ed. 49 2010 7072 7075
131. O. Mahé, I. Dez, V. Levacher, and J.-F. Brière Org. Biomol. Chem. 10 2012 3946 3954
132. P. Maity, and S.D. Lepore Angew. Chem., Int. Ed. 50 2011 8338 8341
133. D. Monge, K.L. Jensen, I. Marín, and K.A. Jørgensen Org. Lett. 13 2011 328 331
134. R.C.D. Brown, and J.F. Keily Angew. Chem., Int. Ed. 40 2001 4496 4498
135. R.A. Bhunnoo, Y. Hu, D.I. Lainé, and R.C.D. Brown Angew. Chem., Int. Ed. 41 2002 3479 3480
136. C. Gioia, F. Fini, A. Mazzanti, L. Bernardi, and A. Ricci J. Am. Chem. Soc. 131 2009 9614 9615
137. T. Kano, A. Yamamoto, S. Song, and K. Maruoka Chem. Commun. 2011 4358 4360
138. T. Kano, A. Yamamoto, S. Song, and K. Maruoka Bull. Chem. Soc. Jpn. 84 2011 1057 1065
139. K. Matoba, H. Kawai, T. Furukawa, A. Kusuda, E. Tokunaga, S. Nakamura, M. Shiro, and N. Shibata Angew. Chem., Int. Ed. 49 2010 5762 5766
140. J. Lacour, and D. Moraleda Chem. Commun. 2009 7073 7089
141. R.J. Phipps, G.L. Hamilton, and F.D. Toste Nat. Chem. 4 2012 603 614
142. V. Rauniyar, A.D. Lackner, G.L. Hamilton, and F.D. Toste Science 334 2011 1681 1684
143. R.J. Phipps, K. Hiramatsu, and F.D. Toste J. Am. Chem. Soc. 134 2012 8376 8379
144. W. Nerinckx, and M. Vandewalle Tetrahedron: Asymmetry 1 1990 265 276
145. K. Shishido, K. Goto, S. Miyoshi, Y. Takaishi, and M. Shibuya J. Org. Chem. 59 1994 406 414
146. J. Qi, A.B. Beeler, Q. Zhang, and J.A. Porco Jr. J. Am. Chem. Soc. 132 2010 13642 13644
147. T. Ooi, M. Takeuchi, and K. Maruoka Synthesis 2001 1716 1718
148. M. Bandini, A. Eichholzer, M. Tragni, and A. Umani-Ronchi Angew. Chem., Int. Ed. 47 2008 3238 3241
149. M. Bandini, A. Bottoni, A. Eichholzer, G.P. Miscione, and M. Stenta Chem. - Eur. J. 16 2010 12462 12473
150. T. Kano, T. Kumano, R. Sakamoto, and K. Maruoka Chem. Sci. 1 2010 499 501
151. T. Kano, T. Kumano, R. Sakamoto, and K. Maruoka Org. Biomol. Chem. 11 2013 271 278
152. R. He, C. Ding, and K. Maruoka Angew. Chem., Int. Ed. 48 2009 4559 4561
153. Y. Park, E. Park, H. Jung, Y.-J. Lee, S.-S. Jew, and H.-G. Park Tetrahedron 67 2011 1166 1170
154. H.P. Shunatona, N. Früh, Y.-M. Wang, V. Rauniyar, and F.D. Toste Angew. Chem. 125 2013 7878 7881
155. L. Hintermann, and C. Dittmer Eur. J. Org. Chem. 28 2012 5573 5584