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Synthesis 2016; 48(16): 2637-2644
DOI: 10.1055/s-0035-1561442
DOI: 10.1055/s-0035-1561442
special topic
Chiral C 2-Symmetric Iodoarene-Catalyzed Asymmetric α-Oxidation of β-Keto Esters
Further Information
Publication History
Received: 24 February 2016
Accepted after revision: 21 March 2016
Publication Date:
11 May 2016 (online)
Abstract
The catalytic asymmetric oxidation of α-substituted β-keto esters promoted by C 2-symmetric iodoarenes as chiral agents and MCPBA as the oxidant is described. By a careful screening of the reaction conditions, promising enantiomeric excesses and moderate-to-good yields were obtained for the synthesis of β-keto esters containing a stereogenic center.
Key words
hypervalent iodine - chiral iodane - oxidations - asymmetric catalysis - carbonyl compoundsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561442.
- Supporting Information
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References
- 1a Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis. Christoffers J, Baro E. Wiley-VCH; Weinheim: 2005
- 1b Trost BM, Jiang C. Synthesis 2006; 369
- 1c Bella M, Gasperi T. Synthesis 2009; 1583
- 1d Quasdorf KW, Overman LE. Nature 2014; 516: 181
- 1e Vetica F, Marcia de Figueiredo R, Orsini M, Tofani D, Gasperi T. Synthesis 2015; 47: 2139
- 2 Nakayama M, Fukuoka Y, Nozaki H, Matsuo A, Hayashi S. Chem. Lett. 1980; 1243
- 3 Aramaki Y, Chiba K, Tada M. Phytochemistry 1995; 38: 1419
- 4 Li J, Liu S.-C, Niu S.-B, Zhuang W.-Y, Che Y.-S. J. Nat. Prod. 2009; 72: 2184
- 5a Christoffers J, Baro A, Werner T. Adv. Synth. Catal. 2004; 346: 143
- 5b Russo A, De Fusco C, Lattanzi A. RSC Adv. 2012; 2: 385
- 6 Acocella MR, Mancheño OG, Bella M, Jørgensen KA. J. Org. Chem. 2004; 69: 8165
- 7 Lu M, Zhu D, Lu Y, Zeng X, Tan B, Xu Z, Zhong G. J. Am. Chem. Soc. 2009; 131: 4562
- 8a Lian M, Li Z, Du J, Meng G, Gao Z. Eur. J. Org. Chem. 2010; 6525
- 8b Lian M, Li Z, Cai Y, Meng Q, Gao Z. Chem. Asian J. 2012; 7: 2019
- 8c Yao H, Lian M, Li Z, Wang Y, Meng Q. J. Org. Chem. 2012; 77: 9601
- 8d De Fusco C, Meninno S, Tedesco C, Lattanzi A. Org. Biomol. Chem. 2013; 11: 896
- 8e Wang Y, Li Z, Xiong T, Zhao J, Meng Q. Synlett 2014; 25: 2155
- 8f Wang Y, Xiong T, Meng Q. Tetrahedron 2015; 71: 85
- 8g Wang Y, Yin H, Qing H, Zhao J, Wu Y, Meng Q. Adv. Synth. Catal. 2016; 358: 737
- 9a Odagi M, Takayama K, Furukori K, Watanabe T, Nagasawa K. Chem. Eur. J. 2013; 19: 16740
- 9b Zou L, Wang B, Mu H, Zhang H, Song Y, Qu J. Org. Lett. 2013; 15: 3106
- 9c Odagi M, Takayama K, Furukori K, Watanabe T, Nagasawa K. Aust. J. Chem. 2014; 67: 1017
- 10a Gong B, Meng Q, Su T, Lian M, Wang Q, Gao Z. Synlett 2009; 2659
- 10b Li Z, Lian M, Yang F, Meng Q, Gao Z. Eur. J. Org. Chem. 2014; 3491
- 11 Wang D, Xu C, Zhang L, Luo S. Org. Lett. 2015; 17: 576
- 12 Cai Y, Lian M, Li Z, Meng Q. Tetrahedron 2012; 68: 7973
- 13a Hypervalent Iodine Chemistry. Modern Developments in Organic Synthesis. In Topics in Current Chemistry. Wirth T. Springer; Berlin: 2003
- 13b Zhdankin VV. Hypervalent Iodine Chemistry Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds. Wiley; Chichester: 2014
- 14a Merritt EA, Olofsson B. Synthesis 2011; 517
- 14b Dong D.-Q, Hao S.-H, Wang Z.-L, Chen C. Org. Biomol. Chem. 2014; 12: 4278
- 15a Richardson RD, Page TK, Altermann S, Paradine SM, French AN, Wirth T. Synlett 2007; 538
- 15b 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
- 15c Farooq U, Schäfer S, Shah AA, Freudendahl DM, Wirth T. Synthesis 2010; 1023
- 15d Yu J, Cui J, Hou X.-S, Liu S.-S, Gao W.-C, Jiang S, Tian J, Zhang C. Tetrahedron: Asymmetry 2011; 22: 2039
- 15e Rodríguez A, Moran WJ. Synthesis 2012; 44: 1178
- 15f Guilbault A.-A, Legault CY. ACS Catal. 2012; 2: 219
- 15g Guilbault A.-A, Basdevant B, Wanie V, Legault CY. J. Org. Chem. 2012; 77: 11283
- 15h Thérien M.-È, Guilbault A.-A, Legault CY. Tetrahedron: Asymmetry 2013; 24: 1193
- 15i Brenet S, Berthiol F, Einhorn J. Eur. J. Org. Chem. 2013; 8094
- 15j Brenet S, Minozzi C, Clarens B, Amiri L, Berthiol F. Synthesis 2015; 47: 3859
- 16a Fujita M, Okuno S, Lee HJ, Sugimura T, Okuyama T. Tetrahedron Lett. 2007; 48: 8691
- 16b Fujita M, Ookubo Y, Sugimura T. Tetrahedron Lett. 2009; 50: 1298
- 17a Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 2175
- 17b Uyanik M, Yasui T, Ishihara K. Tetrahedron 2010; 66: 5841
- 17c Fujita M, Yoshida Y, Miyata K, Wakisaka A, Sugimura T. Angew. Chem. Int. Ed. 2010; 49: 7068
- 17d Fujita M, Mori K, Shimogaki M, Sugimura T. Org. Lett. 2012; 14: 1294
- 17e Shimogaki M, Fujita M, Sugimura T. Eur. J. Org. Chem. 2013; 7128
- 17f Fujita M, Mori K, Shimogaki M, Sugimura T. RSC Adv. 2013; 3: 17717
- 17g Zhang D.-Y, Xu L, Wu H, Gong L.-Z. Chem. Eur. J. 2015; 21: 10314
- 17h Alhalib A, Kamouka S, Moran WJ. Org. Lett. 2015; 17: 1453
- 17i Haubenreisser S, Wöste TH, Martínez C, Ishihara K, Muñiz K. Angew. Chem. Int. Ed. 2016; 55: 413
- 18a Zhdankin VV, Smart JT, Zhao P, Kiprof P. Tetrahedron Lett. 2000; 41: 5299
- 18b Dohi T, Maruyama A, Yoshimura M, Morimoto K, Tohma H, Kita Y. Angew. Chem. Int. Ed. 2005; 44: 6193
- 19a Pihko PM, Pohjakallio A. Synlett 2004; 2215
- 19b Liu X, Sun B, Deng L. Synlett 2009; 1685
- 20a For the preparation of 1a–c, 1e, and 1g,h, see refs. 16a,b.
- 20b For the preparation of 1d, see: Wu H, He Y.-P, Xu L, Zhang D.-Y, Gong L.-Z. Angew. Chem. Int. Ed. 2014; 53: 3466
- 20c For the preparation of 1f, see: Alhalib A, Kamouka S, Moran WJ. Org. Lett. 2015; 17: 1453
- 21 Yin C, Cao W, Lin L, Liu X, Feng X. Adv. Synth. Catal. 2013; 355: 1924
For selected references, see:
For selected references, see:
For selected books on iodine(III) reagents, see:
For seminal reports, see:
For selected catalytic transformations using 1, see:
For selected examples, see: