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Synthesis 2013; 45(4): 452-458
DOI: 10.1055/s-0032-1316843
DOI: 10.1055/s-0032-1316843
paper
Highly Enantioselective Three-Component Reactions of tert-Butyl Diazoacetate with Arylamines and Imines: An Efficient Synthesis of α,β-Bis(arylamino) Acid Derivatives
Further Information
Publication History
Received: 10 November 2012
Accepted after revision: 17 December 2012
Publication Date:
14 January 2013 (online)
Abstract
Enantioselective three-component reactions of tert-butyl diazoacetate with arylamines and imines afford α,β-bis(arylamino) acid derivatives in good yields (56–90%) with high diastereoselectivities (up to >95:5 dr) and excellent enantioselectivities (up to 96% ee).
Key words
multicomponent reaction - tert-butyl diazoacetate - ammonium ylide - imine addition - α,β-diamino acidsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Liqin Jiang and Dan Zhang contributed equally to this work.
- 2a Viso A, Fernandez de la Pradilla R, Garcia A, Flores A. Chem. Rev. 2005; 105: 3167
- 2b Lucet D, Le Gall T, Mioskowski C. Angew. Chem. Int. Ed. 1998; 37: 2580
- 3a Knudsen KR, Risgaard T, Nishiwaki N, Gothelf KV. A. J. Am. Chem. Soc. 2001; 123: 5843
- 3b Nishiwaki N, Knudsen KR, Gothelf KV, Jorgensen KA. Angew. Chem. Int. Ed. 2001; 40: 2992
- 3c Knudsen KR, Jorgensen KA. Org. Biomol. Chem. 2005; 3: 1362
- 3d Hernández-Toribio J, Arrayás RG, Carretero JC. J. Am. Chem. Soc. 2008; 130: 16150
- 3e Chen Z, Morimoto H, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2008; 130: 2170
- 3f Singh A, Johnston JN. J. Am. Chem. Soc. 2008; 130: 5866
- 3g Liang G, Tong MC, Tao H, Wang CJ. Adv. Synth. Catal. 2010; 352: 1851
- 3h Liu X, Deng L, Jiang X, Yan W, Liu C, Wang R. Org. Lett. 2010; 12: 876
- 4a Hossain D, Lavoie G. Synth. Commun. 2012; 42: 1200
- 4b Monillas WH, Yap GP, Theopold KH. Inorg. Chim. Acta 2011; 369: 103
- 4c Hong S, Lee Y, Cho K, Sundaravel K, Cho J, Kim MJ, Shin W, Nam W. J. Am. Chem. Soc. 2011; 133: 11876
-
4d Liu L, Ishida N, Ashida S, Murakami M. Org. Lett. 2011; 13: 1666
- 5a Jung B, Hoveyda AH. J. Am. Chem. Soc. 2012; 134: 1490
-
5b Shigeng G, Tang J, Zhang D, Wang Q, Chen Z, Weng L. J. Organomet. Chem. 2012; 700: 223
- 5c Corberan R, Mszar NW, Hoveyda AH. Angew. Chem. Int. Ed. 2011; 50: 7079
- 5d Albright A, Eddings D, Black R, Welch CJ, Gerasimchuk NN, Gawley RE. J. Org. Chem. 2011; 76: 7341
- 5e Costabile C, Mariconda A, Cavallo L, Longo P, Bertolasi V, Ragone F, Grisi F. Chem. Eur. J. 2011; 17: 8618
-
5f Dastgir S, Coleman KS, Cowley AR, Green ML. H. Organometallics 2010; 29: 4858
- 5g Li J, Stewart IC, Grubbs RH. Organometallics 2010; 29: 3765
- 5h Groaz E, Banti D, North M. Tetrahedron 2008; 64: 204
- 6a Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
- 6b Hartwig JF. Nature 2008; 455: 314
- 6c Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
- 7a Zhu J, Bienaymé H. Multicomponent Reactions . Wiley-VCH; Weinheim: 2005
- 7b Tietze LF, Brasche G, Gericke K. Domino Reactions in Organic Synthesis 2006
- 7c Dömling A. Chem. Rev. 2006; 106: 17
- 7d Wessjohann LA, Rivera DG, Vercillo OE. Chem. Rev. 2009; 109: 796
- 7e Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439
- 7f Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 445: 167
- 7g Enders D, Hüttl MR. M, Grondal C, Raabe G. Nature 2006; 441: 861
- 7h Lu M, Zhu D, Lu Y, Hou Y, Tan B, Zhong G. Angew. Chem. Int. Ed. 2008; 47: 10187 ; Angew. Chem. 2008, 120, 10341
- 7i Li H, Zu L, Xie H, Wang J, Wang W. Chem. Commun. 2008; 5636
- 8a Martin NJ. A, List B. J. Am. Chem. Soc. 2006; 128: 13368
- 8b Liu H, Dagousset G, Masson G, Retailleau P, Zhu J. J. Am. Chem. Soc. 2009; 131: 4598
- 8c Cabrera S, Aleman J, Bolze P, Bertelsen S, Jensen KA. Angew. Chem. Int. Ed. 2008; 47: 121
- 8d Storer RI, Carrera DE, Ni Y, MacMillan DW. C. J. Am. Chem. Soc. 2006; 128: 84
- 8e Jiang J, Yu J, Sun X.-X, Rao QQ, Gong L.-Z. Angew. Chem. Int. Ed. 2008; 47: 2458
- 8f Yamanaka M, Itoh J, Fuchibe K, Akiyama T. J. Am. Chem. Soc. 2007; 129: 6756
- 9a Wang YH, Zhu YG, Chen Z, Mi AQ, Hu WH, Doyle MP. Org. Lett. 2003; 5: 3923
- 9b Jiang J, Xu HD, Xi JB, Ren BY, Lv FP, Guo X, Jiang LQ, Zhang Z, Hu WH. J. Am. Chem. Soc. 2011; 133: 8428
- 10a Hu WH, Xu XF, Zhou J, Liu W, Huang HX, Hu J, Yang LP, Gong LZ. J. Am. Chem. Soc. 2008; 130: 7782
- 10b Xu XF, Zhou J, Yang LP, Hu WH. Chem. Commun. 2008; 6564
- 10c Qian Y, Xu XF, Jiang LQ, Prajapati D, Hu WH. J. Org. Chem. 2010; 75: 7483
- 10d Qian Y, Jing CC, Shi TD, Ji JJ, Tang M, Zhou J, Zhai CW, Hu WH. ChemCatChem 2011; 3: 653
- 11a Yamamoto H, Futatsugi K. Angew. Chem. Int. Ed. 2005; 44: 1924
- 11b Wasilk JE, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
- 11c Park YJ, Park J, Jun C. Acc. Chem. Res. 2008; 41: 222
- 11d Shao ZH, Zhang HB. Chem. Soc. Rev. 2009; 38: 2745
- 11e Zhou J. Chem. Asian J. 2010; 5: 422
- 11f Mukherjee S, List B. J. Am. Chem. Soc. 2007; 129: 11336
- 11g Han ZY, Xiao H, Chen XH, Gong LZ. J. Am. Chem. Soc. 2009; 131: 9182
- 11h Trost BM, McEachern EJ, Toste FD. J. Am. Chem. Soc. 1998; 120: 12702
- 12a Terada M, Machioka K, Sorimachi K. Angew. Chem. Int. Ed. 2009; 48: 2553 ; Angew. Chem. 2009, 121, 2591
- 12b Lu M, Zhu D, Lu Y, Zeng X, Tan B, Xu Z, Zhong GF. J. Am. Chem. Soc. 2009; 131: 4562
- 12c Akiyama T, Itoh J, Yokota K, Fuchibe K. Angew. Chem. Int. Ed. 2004; 43: 1566 ; Angew. Chem. 2004, 116, 1592
- 12d Ref. 11g.
- 12e Zeng X, Xu Z, Lu M, Zhong G. Org. Lett. 2009; 11: 3036
- 12f Akiyama T. Chem. Rev. 2007; 107: 5744
- 12g Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
- 13 Crystal data for 8c, see the Supporting Information. CCDC 908163 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax +44(1223)336033; or deposit@ ccdc.cam.ac.uk].
- 14 Myhre PC, Maxey CT, Bebout DC, Swedberg SH, Petersen BL. J. Org. Chem. 1990; 55: 3417
- 15 Shiino M, Watanabe Y, Umezawa K. Bioorg. Med. Chem. 2001; 9: 1233
- 16a Hu WH, Zhou J, Xu XF, Liu WJ, Gong LZ. Org. Synth. 2011; 88: 406
-
16b Zhu SS, Cefalo DR, La DS, Jamieson JY, Davis WM, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1999; 121: 8251
- 16c Klussmann M, Ratjen L, Hoffmann S, Wakchaure V, Goddard R, List B. Synlett 2010; 2189
Review on vicinal diamines:
For recent reviews on multicomponent reactions, see:
For recent examples of multicomponent reactions, see:
Selected examples of recent progress in AMCRs:
For cooperative catalysis to enhance reaction selectivity, see reviews:
Selected examples:
Selected examples of chiral Brønsted acid catalyzed addition reactions to imines:
For reviews, see:
For preparation of 1a–i:
For preparation of 1j: