Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(05): 587-603
DOI: 10.1055/s-0034-1379892
DOI: 10.1055/s-0034-1379892
review
Reagent and Catalyst Design for Asymmetric Hypervalent Iodine Oxidations
Further Information
Publication History
Received: 30 October 2014
Accepted after revision: 20 November 2014
Publication Date:
28 January 2015 (online)
Abstract
In this review are compiled the different possible transformations using environmentally benign chiral hypervalent iodine reagents and catalysts. Herein is presented an overview of asymmetric oxidation of sulfides to sulfoxides, oxidation of alkenes, α-functionalization of carbonyl compounds and dearomatization reactions.
1 Introduction
2 Chiral Hypervalent Iodine Reagents
3 Oxidation of Sulfides to Sulfoxides
4 Oxidation of Alkenes
5 α-Functionalization of Carbonyl Compounds
6 Dearomatization Reactions
7 Conclusion
-
References
- 1 Willgerodt C. J. Prakt. Chem. 1886; 33: 154
- 2 Varvoglis A. Tetrahedron 2010; 66: 5739
- 3 Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
- 4 Varvoglis A. Tetrahedron 1997; 53: 1179
- 5 Finkbeiner P, Nachtsheim BJ. Synthesis 2013; 45: 979
- 6 Wirth T. Angew. Chem. Int. Ed. 2005; 44: 3656
- 7 Brown M, Farid U, Wirth T. Synlett 2013; 24: 424
- 8 Ochiai M. Chem. Rec. 2007; 7: 12
-
9 Merritt EA, Berit O. Angew. Chem. Int. Ed. 2009; 48: 9052
- 10 The Organic Chemistry of Polycoordinated Iodine . Varvoglis A. VCH Publishers Inc; New York: 1992
- 11 Hypervalent Iodine Chemistry. Zhdankin VV. Wiley; Chichester: 2014
- 12 Uyanik M, Okamoto H, Yasui T, Ishihara K. Science 2010; 328: 1376
- 13 Mizar P, Laverny A, El-Sherbini M, Farid U, Brown M, Malmedy F, Wirth T. Chem. Eur. J. 2014; 20: 9910
- 14 Prakash O, Singh SP. Aldrichimica Acta 1994; 27: 15
- 15 Pohnert G. J. Prakt. Chem. 2000; 342: 731
- 16 Duschek A, Kirsch SF. Angew. Chem. Int. Ed. 2011; 50: 1524
- 17 Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
- 18a Ngatimin M, Lupton DW. Aust. J. Chem. 2010; 63: 653
- 18b Liang H, Ciufolini MA. Angew. Chem. Int. Ed. 2011; 50: 11849
- 18c Uyanik M, Ishihara K. J. Synth. Org. Chem. Jpn. 2012; 70: 1116
- 18d Farid U, Wirth T. Stereoselective Reactions with Hypervalent Iodine Compounds . In Asymmetric Synthesis – The Essentials. Bräse S, Christmann C. Wiley–VCH; Weinheim: 2012: 197-203
- 18e Parra A, Reboredo S. Chem. Eur. J. 2013; 19: 17244
- 19 Imamoto T, Koto H. Chem. Lett. 1986; 967
- 20 Ray DG. III, Koser GF. J. Org. Chem. 1992; 57: 1607
- 21 Ray DG. III, Koser GF. J. Am. Chem. Soc. 1990; 112: 5672
- 22 Xia M, Chen Z.-C. Synth. Commun. 1997; 27: 1315
- 23 Wirth T, Hirt UH. Tetrahedron: Asymmetry 1997; 8: 23
- 24 Ochiai M, Takeuchi Y, Katayama T, Sueda T, Miyamoto K. J. Am. Chem. Soc. 2005; 127: 12244
- 25 Dohi T, Maruyama A, Yoshimura M, Morimoto K, Tohma H, Kita Y. Angew. Chem. Int. Ed. 2005; 44: 6193
- 26 Richardson RD, Page TK, Altermann S, Paradine SM, French AN, Wirth T. Synlett 2007; 538
- 27 O’Mahony GE, Ford A, Maguire A. J. Sulfur Chem. 2013; 34: 301 ; and references cited therein
- 28 Tohma H, Takizawa S, Watanabe H, Fukuoka Y, Maegawa T, Kita Y. J. Org. Chem. 1999; 64: 3519
- 29 Tohma H, Takizawa S, Morioka H, Maegawa T, Kita Y. Chem. Pharm. Bull. 2000; 48: 445
- 30 Ozanne-Beaudenon A, Quideau S. Tetrahedron Lett. 2006; 47: 5869
- 31 Hatzigrigoriou E, Varvoglis A, Bakola-Christianopoulou M. J. Org. Chem. 1990; 55: 315
- 32 Zhdankin VV, Smart JT, Zhao P, Kiprof P. Tetrahedron Lett. 2000; 41: 5299
- 33 Ladziata U, Carlson J, Zhdankin VV. Tetrahedron Lett. 2006; 47: 6301
- 34 Altermann SM, Schäfer S, Wirth T. Tetrahedron 2010; 66: 5902
-
35 Katsuki T, Sharpless KB. J. Am. Chem. Soc. 1980; 102: 5974
-
36 Jacobsen EN, Markò I, Mungall WS, Schröder G, Sharpless KB. J. Am. Chem. Soc. 1988; 110: 1968
- 37 Hirt UH, Spingler B, Wirth T. J. Org. Chem. 1998; 63: 7674
- 38 Hirt UH, Schuster MF. H, Frenh AN, Wiest OG, Wirth T. Eur. J. Org. Chem. 2001; 1569
- 39 Fujita M, Wakita M, Sugimura T. Chem. Commun. 2011; 47: 3983
- 40 Koposov AY, Boyarskikh VV, Zhdankin VV. Org. Lett. 2004; 6: 3613
- 41 Boye AC, Meyer D, Ingison CK, French AN, Wirth T. Org. Lett. 2003; 5: 2157
- 42 Fujita M, Okuno S, Lee HJ, Sugimura T, Okuyama T. Tetrahedron Lett. 2007; 48: 8691
- 43 Fujita M, Yoshida Y, Miyata K, Wakisaka A, Sugimura T. Angew. Chem. Int. Ed. 2010; 49: 7068
- 44 Fujita M, Mori K, Shimogaki M, Sugimura T. Org. Lett. 2012; 14: 1294
- 45 Fujita M, Mori K, Shimogaki M, Sugimura T. RSC Adv. 2013; 3: 17717
- 46 Shimogaki M, Fujita M, Sugimura T. Eur. J. Org. Chem. 2013; 7128
- 47 Takesue T, Fujita M, Sugimura T, Akutsu H. Org. Lett. 2014; 16: 4634
- 48a Brown KJ, Berry MS, Watermann KC, Lingenfelter D, Murdoch JR. J. Am. Chem. Soc. 1984; 106: 4717
- 48b Richardson RD, Desaize M, Wirth T. Chem. Eur. J. 2007; 13: 6745
- 49 Deng Q.-H, Wang J.-C, Xu Z.-J, Zhou C.-Y, Che C.-M. Synthesis 2011; 2959
- 50 Röben C, Souto JA, González Y, Lishchynskyi A, Muñiz K. Angew. Chem. Int. Ed. 2011; 50: 9478
- 51 Röben C, Souto JA, Escudero-Adán EC, Muñiz K. Org. Lett. 2013; 15: 1008
- 52 Farid U, Wirth T. Angew. Chem. Int. Ed. 2012; 51: 3462
- 53 Ngatimin M, Gartshore CJ, Kindler JP, Naidu S, Lupton DW. Tetrahedron Lett. 2009; 50: 6008
- 54 Nicolaou KC, Simmons NL, Ying Y, Heretsch PM, Chen JS. J. Am. Chem. Soc. 2011; 133: 8134
- 55 Kong W, Feige P, de Haro T, Nevado C. Angew. Chem. Int. Ed. 2013; 52: 2469
- 56 Suzuki S, Kamo T, Fukushi K, Hiramatsu T, Tokunaga E, Dohi T, Kita Y, Shibata N. Chem. Sci. 2014; 5: 2754
- 57 Farid U, Malmedy F, Claveau R, Albers L, Wirth T. Angew. Chem. Int. Ed. 2013; 52: 7018
- 58 Purkait N, Okumura S, Souto JA, Muñiz K. Org. Lett. 2014; 16: 4750
- 59 Merritt EA, Olofsson B. Synlett 2011; 517
- 60 Dong D.-Q, Hao S.-H, Wang Z.-L, Chen C. Org. Biomol. Chem. 2014; 12: 4278
- 61 Altermann SM, Richardson RD, Page TK, Schmidt RK, Holland E, Mohammed U, Paradine SM, French AN, Richter C, Bahar AM, Witulski B, Wirth T. Eur. J. Org. Chem. 2008; 5315
- 62 Farooq U, Schäfer S, Ali Shah A.-U.-H, Freudendahl DM, Wirth T. Synthesis 2010; 1023
- 63 Yu J, Cui J, Hou X.-S, Liu S.-S, Gao W.-C, Jiang S, Tian J, Zhang C. Tetrahedron: Asymmetry 2011; 22: 2039
- 64 Rodríguez A, Moran WJ. Synthesis 2012; 44: 1178
- 65 Guibault A.-A, Legault CY. ACS Catal. 2012; 2: 219
- 66 Guibault A.-A, Basdevant B, Wanie V, Legault CY. J. Org. Chem. 2012; 77: 11283
- 67 Thérien M.-E, Guibault A.-A, Legault CY. Tetrahedron: Asymmetry 2013; 24: 1193
- 68 Brenet S, Berthiol F, Einhorn J. Eur. J. Org. Chem. 2013; 8094
- 69 Mizar P, Wirth T. Angew. Chem. Int. Ed. 2014; 53: 5993
- 70 Ochiai M, Kitagawa Y, Takayama N, Takaoka Y, Shiro M. J. Am. Chem. Soc. 1999; 121: 9233
- 71 Fernández González D, Brand JP, Mondière R, Waser J. Adv. Synth. Catal. 2013; 355: 1631
- 72 Wu X, Shirakawa S, Maruoka K. Org. Biomol. Chem. 2014; 12: 5388
- 73 Siegel A, Antony F. Monatsh. Chem. 1955; 86: 292
- 74 Roche SP, Porco JA. Jr. Angew. Chem. Int. Ed. 2011; 50: 4068
- 75 Pouységu L, Deffieux D, Quideau S. Tetrahedron 2010; 66: 2235
- 76 For a review concerning catalytic asymmetric dearomatization reactions, see: Zhuo C.-X, Zhang W, You S.-L. Angew. Chem. Int. Ed. 2012; 51: 12662
- 77 Dohi T, Maruyama A, Takenaga N, Senami K, Minamitsuji Y, Fujioka H, Caemmerer SB, Kita Y. Angew. Chem. Int. Ed. 2008; 47: 3787
- 78 Dohi T, Kita Y, Maruyama A. Jpn. Kokai Tokkyo Koho 2009149564A, 2009
- 79 Dohi T, Takenaga N, Nakae T, Toyoda Y, Yamasaki M, Shiro M, Fujioka H, Maruyama A, Kita Y. J. Am. Chem. Soc. 2013; 135: 4558
- 80 Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 2175
- 81 Uyanik M, Yasui T, Ishihara K. Tetrahedron 2010; 66: 5841
- 82 Buffeteau T, Cavagnat D, Chénedé A. Angew. Chem. Int. Ed. 2009; 48: 4605
- 83 Boppisetti JK, Birman VB. Org. Lett. 2009; 11: 1221
- 84 Gagnepain J, Méreau R, Dejugnac D, Léger J.-M, Castet F, Deffieux D, Pouységu L, Quideau S. Tetrahedron 2007; 63: 6493
- 85 Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2013; 52: 9215
- 86 Bosset C, Coffinier R, Peixoto PA, El Assal M, Miqueu K, Sotiropoulos J.-M, Pouységu L, Quideau S. Angew. Chem. Int. Ed. 2014; 53: 9860
- 87 Volp K, Harned AM. Chem. Commun. 2013; 49: 3001
For reviews on chiral hypervalent iodine reagents and catalysts, see: