Chiral hypervalent iodine reagents: Synthesis and reactivity

Chemistry - A European Journal

Volumn 19, Issue 51, 2013, Pages 17244-17260

  Parra, Alejandro ^a   Reboredo, Silvia ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

asymmetric synthesis; hypervalent iodine; organocatalysis; oxidation dearomatization

Indexed keywords

ASYMMETRIC SYNTHESIS; CATALYTIC QUANTITIES; DEAROMATIZATION; ENANTIOSELECTIVE TRANSFORMATION; HYPERVALENT IODINE; HYPERVALENT IODINE CHEMISTRY; HYPERVALENT IODINE REAGENTS; ORGANOCATALYSIS;

CATALYSTS; ENANTIOSELECTIVITY; REACTION KINETICS;

IODINE;

EID: 84890123981     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302220     Document Type: Review

References (170)

1. T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691-1693
2. Q.-L. Zhou, in Privileged Chiral Ligand Catalysts, Wiley-VCH, Weinheim (Germany), 2011.
3. Comprensive Asymmetric Catalysis, Vol I-III. (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, New York (USA), 1999
4. New Frontier in Asymmetric Synthesis (Eds.:, K. Mikami, M. Lautens,), Wiley, Hoboken (USA), 2007.
5. A. Berkessel, H. Göger, in Asymmetric Organocatalysis, Wiley-VCH, Weinheim (Germany), 2005
6. P. I. Dalko, in Enantioselective Organocatalysis, Wiley-VCH, Weinheim (Germany), 2007
7. A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416-5470
8. D. W. C. MacMillan, Nature 2008, 455, 304-308
9. C. F. Barbas III, Angew. Chem. 2008, 120, 44-50
10. Angew. Chem. Int. Ed. 2008, 47, 42-47
11. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232-6265
12. Angew. Chem. Int. Ed. 2008, 47, 6138-6171
13. A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716-4739
14. Angew. Chem. Int. Ed. 2008, 47, 4638-4660
15. E. N. Jacobsen, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2010, 107, 20618-20619
16. Science of Synthesis Asymmetric Organocatalysi,s Vol. 2 (Eds.:, B. List, K. Maruoka,), Thieme, Stuttgart (Germany), 2012
17. A. Parra, S. Reboredo, J. Alemán, Angew. Chem. 2012, 124, 9872-9874
18. Angew. Chem. Int. Ed. 2012, 51, 9734-9736
19. J. Alemán, S. Cabrera, Chem. Soc. Rev. 2013, 42, 774-793.
20. C. Bolm, Med. Res. Rev. 1999, 19, 348-356
21. Transition Metals for Organic Synthesis (Eds.:, M. Beller, C. Bolm,), Wiley-VCH, Weinheim (Germany), 2004
22. T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329-2364
23. S. S. Stahl, Science 2005, 309, 1824-1826
24. Modern Oxidation Methods, 2 nd ed., (Ed.: J.-E. Bäckvall,), Wiley-VCH, Weinheim (Germany), 2010; for a recent review on asymmetric oxidation, see
25. C. A. Sandoval, R. Noyori, in Organic Chemistry-Breakthroughs and Perspectives (Eds.:, K. Ding, L.-X. Dai,), Wiley-VCH, Weinheim (Germany), 2012, pp. 335-366.
26. Industrial Biotransformations, 2 nd ed., (Eds.: A. Liese, K. Seelbach, C. Wandrey,), Wiley-VCH, Weinheim (Germany), 2006
27. F. Hollmann, I. W. C. E. Arends, K. Buehler, A. Schallmey, B. Buehler, Green Chem. 2011, 13, 226-265
28. D. Romano, R. Villa, F. Molinari, ChemCatChem 2012, 4, 739-749
29. G. de Gonzalo, A. A. Orden, F. R. Bisogno, Curr. Org. Chem. 2012, 16, 2598-2612.
30. H. Adolfsson, Angew. Chem. 2005, 117, 3404-3406
31. Angew. Chem. Int. Ed. 2005, 44, 3340-3342
32. J. Rosen, Chemtracts 2005, 18, 65-71
33. Z. Wang, Z. Jiang, Asian J. Chem. 2010, 22, 4141-4149
34. J. G. de Vries, N. Mrŝic̈, Catal. Sci. Technol. 2011, 1, 727-735
35. M. Rueping, J. Dufour, F. R. Schoepke, Green Chem. 2011, 13, 1084-1105 and references cited therein.
36. C. Willgerodt, J. Prakt. Chem. 1886, 33, 154-160.
37. A. Varvoglis, Tetrahedron 2010, 66, 5739-5744; for an introduction to hypervalent chemistry of elements from Groups 15-18 see
38. J. I. Musher, Angew. Chem. 1969, 81, 68-83
39. Angew. Chem. Int. Ed. Engl. 1969, 8, 54-68; for general reviews of hypervalent iodine chemistry, see
40. "Hypervalent Iodine Chemistry: Modern Development in Organic Synthesis"in Topics in Current Chemistry, Vol. 224; (Ed.:, T. Wirth,), Springer, Berlin (Germany), 2003
41. T. Wirth, Angew. Chem. 2005, 117, 3722-3731
42. Angew. Chem. Int. Ed. 2005, 44, 3656-3665
43. U. Ladziata, V. V. Zhdankin, Synlett 2007, 527-537
44. S. Quideau, L. Pouységu, D. Deffieux, Synlett 2008, 467-495
45. E. A. Merritt, B. Olofsson, Angew. Chem. 2009, 121, 9214-9234
46. Angew. Chem. Int. Ed. 2009, 48, 9052-9070
47. D. Fernández-González, F. Benfatti, J. Waser, ChemCatChem 2012, 4, 955-958
48. M. S. Yusubov, V. V. Zhdankin, Curr. Org. Synth. 2012, 9, 247-272
49. M. Brown, U. Farid, T. Wirth, Synlett 2013, 24, 424-431; for reviews regarding to stereoselective transformations mediated by hypervalent iodines, see
50. A. N. French, S. Bissmire, T. Wirth, Chem. Soc. Rev. 2004, 33, 354-362
51. E. A. Merritt, B. Olofsson, Synthesis 2011, 517-538
52. Y. Kita, T. Dohi, K. Morimoto, J. Synth. Org. Chem. Jpn. 2011, 69, 1241-1250; for reviews of the use of chiral hypervalent iodine reagents, see
53. M. Ngatimin, D. W. Lupton, Aust. J. Chem. 2010, 63, 653-658
54. H. Liang, M. A. Ciufolini, Angew. Chem. 2011, 123, 12051-12053
55. Angew. Chem. Int. Ed. 2011, 50, 11849-11851
56. U. Farid, T. Wirth, Asymmetric Synthesis II (Eds.:, M. Christmann, S. Bräse,) Wiley-VCH, Weinheim (Germany), 2012, pp. 197-203.
57. P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178
58. V. Zhdankin, P. J. Stang, Tetrahedron 1998, 54, 10927-2964
59. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584
60. M. A. Ciufolini, N. A. Braun, S. Canesi, M. Ousmer, J. Chang, D. Chai, Synthesis 2007, 3759-3772
61. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299-5358
62. M. Uyanik, K. Ishihara, Chem. Commun. 2009, 2086-2085
63. V. V. Zhdankin, ARKIVOC (Gainesville, FL, U.S.) 2009, 1-62
64. M. S. Yusubov, A. V. Maskaev, V. V. Zhdankin, ARKIVOC (Gainesville, FL, U.S.) 2011, 370-409.
65. A. Varvoglis, in The Organic Chemistry of Polycoordinated Iodine, VCH, Weinheim (Germany), 1992
66. T. Wirth, Angew. Chem. 2001, 113, 2893-2895
67. Angew. Chem. Int. Ed. 2001, 40, 2812-2814
68. T. Wirth, in Organic Synthesis Highlights V, (Eds.:, H.-G. Schmalz, T. Wirth,), Wiley-VCH, Weinheim (Germany) 2003, pp. 144-150
69. U. Ladziata, V. V. Zhdankin, ARKIVOC (Gainesville, FL, U.S.) 2006, 9, 26-58
70. V. Zhdankin, J. Org. Chem. 2011, 76, 1185-1197; for a review regarding the use of IBX, see
71. A. Duschek, S. F. Kirsch, A. Duschek, S. F. Kirsch, Angew. Chem. 2011, 123, 1562-1590
72. Angew. Chem. Int. Ed. 2011, 50, 1524-1552.
73. O. Prakash, S. P. Singh, Aldrichimica Acta 1994, 27, 15-23; for review on the use of PIFA, see
74. G. Pohnert, J. Prakt. Chem. 2000, 342, 731-734
75. I. Tellitu, E. Dominguez, Synlett 2012, 23, 2165-2175.
76. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156.
77. For the first example of chiral hypervalent iodine reagent ever reported, see:, R. Pribram, Justus Liebigs Ann. Chem. 1907, 351, 481-485.
78. T. Imamoto, H. Koto, Chem. Lett. 1986, 967-968.
79. D. G. Ray III, G. F. Koser, J. Org. Chem. 1992, 57, 1607-1610.
80. D. G. Ray III, G. F. Koser, J. Am. Chem. Soc. 1990, 112, 5672-5673.
81. M. Xia, Z.-C. Chen, Synth. Commun. 1997, 27, 1321-1326.
82. E. Hatzigrigoriou, A. Varvoglis, M. Bakola-Christianopoulou, J. Org. Chem. 1990, 55, 315-318.
83. H. Tohma, S. Takizawa, H. Watanabe, Y. Fukuoka, T. Maegawa, Y. Kita, J. Org. Chem. 1999, 64, 3519-3523.
84. R. D. Richardson, T. Wirth, Angew. Chem. 2006, 118, 4510-4512
85. Angew. Chem. Int. Ed. 2006, 45, 4402-4404
86. M. Ochiai, Chem. Rec. 2007, 7, 12-23
87. M. Ochiai, K. Miyamoto, Eur. J. Org. Chem. 2008, 4229-4239
88. T. Dohi, Y. Kita, Chem. Commun. 2009, 2073-2085. For selected examples, see
89. M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda, K. Miyamoto, J. Am. Chem. Soc. 2005, 127, 12244-12245
90. T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, Y. Kita, Angew. Chem. 2005, 117, 6349-6352
91. Angew. Chem. Int. Ed. 2005, 44, 6193-6196
92. A. P. Thottumkara, M. S. Bowsher, T. K. Vinod, Org. Lett. 2005, 7, 2933-2936
93. Y. Yamamoto, H. Togo, Synlett 2006, 798-800
94. J. Sheng, X. Li, M. Tang, B. Gao, G. Huang, Synthesis 2007, 1165-1168
95. A. Yoshimura, K. R. Middleton, M. W. Luedtke, C. Zhu, V. V. Zhdankin, J. Org. Chem. 2012, 77, 11399-11404
96. C. Zhu, L. Ji, Q. Zhang, Y. Wei, Can. J. Chem. 2010, 88, 362-366
97. A. Rodríguez, W. J. Moran, Org. Lett. 2011, 13, 2220-2223.
98. H. Tohma, S. Takizawa, H. Motioka, T. Maegawa, Y. Kita, Chem. Pharm. Bull. 2000, 48, 445-446.
99. V. V. Zhdankin, J. T. Smart, P. Zhao, P. Kiprof, Tetrahedron Lett. 2000, 41, 5299-5302.
100. U. Ladziata, J. Carlson, V. V. Zhdankin, Tetrahedron Lett. 2006, 47, 6301-6304.
101. S. M. Altermann, S. Schäfer, T. Wirth, Tetrahedron 2010, 66, 5902-5907.
102. A. R. Pape, K. P. Kaliappan, E. P. Kündig, Chem. Rev. 2000, 100, 2917-2940
103. R. A. Johnson, Organic Reactions, Vol. 63, Wiley, New York (USA), 2004, pp. 117-264
104. F. Lõpez-Ortiz, M. J. Iglesias, I. Fernández, C. M. Andújar-Sánchez, G. R. Gõmez, Chem. Rev. 2007, 107, 1580-1691
105. T. Hudlicky, J. W. Reed, Synlett 2009, 685-703; for an excellent review concerning dearomatization reactions in total synthesis of natural products, see
106. S. P. Roche, J. A. Porco Jr., Angew. Chem. 2011, 123, 4154-4179
107. Angew. Chem. Int. Ed. 2011, 50, 4068-4093
108. C.-X. Zhuo, W. Zhang, S.-L You, Angew. Chem. 2012, 124, 12834-12858
109. Angew. Chem. Int. Ed. 2012, 51, 12662-12686 and references cited therein.
110. D. Magdziak, S. J. Meek, T. R. R. Pettus, Chem. Rev. 2004, 104, 1383-1430
111. S. E. Bode, D. Drochner, M. Miller, Angew. Chem. 2007, 119, 6020-6024
112. Angew. Chem. Int. Ed. 2007, 46, 5916-5920; for an excellent review concerning phenols dearomatization in the total synthesis of natural products, see
113. L. Pouységu, D. Deffieux, S. Quideau, Tetrahedron 2010, 66, 2235-2261 and references cited therein.
114. S. Quideua, in Modern Arene Chemistry (Ed.:, D. Astruc,), Wiley-VCH, Weinheim (Germany), 2002, pp. 539-573; for a seminal work in the phenol dearomatiozation by using a hypervalent iodine reagent, see
115. A. Siegel, F. Antony, Monatsh. Chem. 1955, 86, 292-300.
116. T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita, Angew. Chem. 2008, 120, 3847-3850
117. Angew. Chem. Int. Ed. 2008, 47, 3787-3790; for a synthesis of o-quinones monoacetals using chiral alcohols mediated by PIDA, see
118. L. Pouységu, S- Chassaing, D. Dejugnac, A.-M- Lamidey, K. Miqueu, J.-M. Sotiropoulos, S. Quideau, Angew. Chem. 2008, 120, 3608-3611
119. Angew. Chem. Int. Ed. 2008, 47, 3552-3555.
120. T. Dohi, Y. Kita, Kagaku 2006, 61, 68-69
121. T. Dohi, A. Maruyama, Y. Minamitsuji, N. Takenaga, Y. Kita, Chem. Commun. 2007, 1224-1226.
122. T. Dohi, N. Takenaga, T. Nakae, Y. Yamasaki, M. Shiro, H. Fujioka, A. Maruyama, Y. Kita, J. Am. Chem. Soc. 2013, 135, 4558-4566.
123. J. K. Boppisetti, V. B. Birman, Org. Lett. 2009, 11, 1221-1223; for a racemic synthesis of o-quinols and [4+2] cyclodimerization of phenols catalyzed by hypervalent iodine chemistry, see
124. N. Lebrasseur, J. Gagnepain, A. Ozanne-Beaudenon, J.-M. Légerm, S. Quideua, J. Org. Chem. 2007, 72, 6280-6283.
125. S. Quideau, G. Lyvinec, M. Marguerit, K. Bathany, A. Ozanne-Beaudenon, T. Buffeteau, D. Cavagnat, A. Chénedé, Angew. Chem. 2009, 121, 4675-4679
126. Angew. Chem. Int. Ed. 2009, 48, 4605-4609.
127. M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. 2010, 122, 2221-2223
128. Angew. Chem. Int. Ed. 2010, 49, 2175-2177
129. M. Uyanik, T. Yasui, K. Ishihara, Tetrahedron 2010, 66, 5841-5851.
130. K. A. Volp, A. M. Harned, Chem. Commun. 2013, 49, 3001-3003.
131. M. Ochiai, Y. Takaoka, Y. Masaki, Y. Nagao, M. Shiro, J. Am. Chem. Soc. 1990, 112, 5677-5678; for the first chiral alkynyl(phenyl)iodonium salts, see
132. T. Kitamura, C. H. Lee, Y. Taniguchi, Y. Fujiwara, M. Matsumoto, Y. Sano, J. Am. Chem. Soc. 1997, 119, 619-620
133. M. Ochiai, Y. Kitagawa, N. Takayama, Y. Takaoka, M. Shiro, J. Am. Chem. Soc. 1999, 121, 9233-9234.
134. N. Jalalian, B. Olofsson, Tetrahedron 2010, 66, 5793-5800.
135. G. F. Koser, R. H. Wettbach, J. Org. Chem. 1977, 42, 1476-1478
136. G. F. Koser, A. G. Relenyi, A. N. Kalos, L. Rebrovic, R. H. Wettbach, J. Org. Chem. 1982, 47, 2487-2489.
137. R. D. Richardson, T. K. Page, S. Altermann, S. M. Paradine, A. N. French, T. Wirth, Synlett 2007, 538-542.
138. S. M. Altermann, R. D. Richardson, T. K. Page, R. K. Schmidt, E. Holland, U. Mohammed, S. M. Paradine, A. N. French, C. Richter, A. M. Bahar, B. Witulski, T. Wirth, Eur. J. Org. Chem. 2008, 5315-5328.
139. U. Farooq, S. Schäfer, A.-U.-H. Ali Shah, D. M. Freudendahl, T. Wirth, Synthesis 2010, 1023-1029.
140. A. Rodríguez, W. J. Moran, Synthesis 2012, 44, 1178-1182.
141. A.-A. Guilbault, B. Basdevant, V. Wanie, C. Y. Legault, J. Org. Chem. 2012, 77, 11283-11295
142. A.-A. Guilbault, C. Y. Legault, ACS Catal. 2012, 2, 219-222.
143. T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26.
144. T. Wirth, Angew. Chem. 1995, 107, 1872-1873
145. Angew. Chem. Int. Ed. Eng. 1995, 34, 1726-1728
146. T. Wirth, K. J. Kulicke, G. Fragale, J. Org. Chem. 1996, 61, 2686-2689.
147. U. H. Hirt, B. Spingler, T. Wirth, J. Org. Chem. 1998, 63, 7674-7679
148. U. H. Hirt, M. F. H. Schuster, A. N. French, O. G. Wiest, T. Wirth, Eur. J. Org. Chem. 2001, 1569-1579.
149. A. C. Boye, D. Meyer, C. K. Ingison, A. N. French, T. Wirth, Org. Lett. 2003, 5, 2157-2159.
150. A. Y. Koposov, V. V. Boyarskikih, V. V. Zhdankin, Org. Lett. 2004, 6, 3613-3615.
151. M. Fujita, S. Okuno, H. J. Lee, T. Sugimura, T. Okuyama, Tetrahedron Lett. 2007, 48, 8691-8694
152. M. Fujita, Y. Ookubo, T. Sugimura, Tetrahedron Lett. 2009, 50, 1298-1300.
153. M. Ngatimin, C. J. Gartshore, J. P. Kindler, S. Naidu, D. W. Lupton, Tetrahedron Lett. 2009, 50, 6008-6011.
154. M. Fujita, Y. Yoshida, K. Miyata, A. Wakisaka, T. Sugimura, Angew. Chem. 2010, 122, 7222-7225
155. Angew. Chem. Int. Ed. 2010, 49, 7068-7071.
156. M. Fujita, M. Wakita, T. Sugimura, Chem. Commun. 2011, 47, 3983-3985.
157. C. Röben, J. A. Souto, Y. González, A. Lischynskyi, K. Muñiz, Angew. Chem. 2011, 123, 9650-9654
158. Angew. Chem. Int. Ed. 2011, 50, 9478-9482.
159. For a aziridination reaction using hypervalent iodine(III) reagent, see:, R. D. Richardson, M. Desaize, T. Wirth, Chem. Eur. J. 2007, 13, 6745-6754.
160. Q.-H. Deng, J.-C. Wang, Z.-J. Xu, C.-Y. Zhou, C.-M. Che, Synthesis 2011, 2959-2967.
161. U. Farid, T. Wirth, Angew. Chem. 2012, 124, 3518-3522
162. Angew. Chem. Int. Ed. 2012, 51, 3462-3465.
163. M. Fujita, K. Mori, M. Shimogaki, T. Sugimura, Org. Lett. 2012, 14, 1294-1297.
164. W. Kong, P. Feige, T. de Haro, C. Nevado, Angew. Chem. 2013, 125, 2529-2533
165. Angew. Chem. Int. Ed. 2013, 52, 2469-2473.
166. C. Röben, J. A. Souto, E. C. Escudero-Adán, K. Muñiz, Org. Lett. 2013, 15, 1008-1011.
167. U. Farid, F. Malmedy, R. Claveau, L. Albers, T. Wirth, Angew. Chem. 2013, 125, 7156-7160
168. Angew. Chem. Int. Ed. 2013, 52, 7018-70227; for a seminal work concerning this transformation in achiral version, see
169. R. M. Moriarty, J. S. Khosrowshahi, O. Parakash, Tetrahedron Lett. 1985, 26, 2961-2964; for a similar oxidative rearrangement in racemic version, see
170. F. V. Singh, J. Rehbein, T. Wirth, ChemistryOpen 2012, 1, 245-250.