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 2017; 49(07): 1519-1530
DOI: 10.1055/s-0036-1588408
DOI: 10.1055/s-0036-1588408
feature
Michael Addition of Oxindoles to N-(2-tert-Butylphenyl)maleimides: Efficient Desymmetrization for the Synthesis of Atropisomeric Succinimides with Quaternary and Tertiary Stereocenters
Further Information
Publication History
Received: 11 January 2017
Accepted after revision: 13 January 2017
Publication Date:
08 February 2017 (online)
Abstract
The desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael reaction of N-(tert-butoxycarbonyl)-3-phenyloxindoles leading to the corresponding axially chiral succinimides in high yields. The use of a squaramide cinchonidine organocatalyst was fundamental to achieve the simultaneous remote control of the stereogenic axis and adjacent quaternary and tertiary stereocenters.
Key words
desymmetrization - stereogenic axis - oxindoles - atropisomerism - Michael addition - organocatalysisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588408.
- Supporting Information
-
References
- 1a Christie GH, Kenner JH. J. Chem. Soc. 1922; 121: 614
- 1b Ōki M. Top. Stereochem. 1983; 14: 1
- 1c Eliel EL, Wilen SH. Stereochemistry of Organic Compounds . Wiley; New York: 1994
- 1d For a detailed review, see: Kumarasamy E, Raghunathan R, Sibi MP, Sivaguru J. Chem. Rev. 2015; 115: 11239
- 1e Wencel-Delord J, Panossian A, Leroux FR, Colobert F. Chem. Soc. Rev. 2015; 44: 3418
- 1f Bringmann G, Price Mortimer AJ, Keller PA, Gresser MJ, Garner J, Breuning M. Angew. Chem. Int. Ed. 2005; 44: 5384
- 2a Bencivenni G. Synlett 2015; 26: 1915
- 2b Shirakawa S, Liu S, Kaneko S. Chem. Asian J. 2016; 11: 330
- 2c Staniland S, Adams RW, McDouall JJ. W, Maffucci I, Contini A, Grainger DM, Turner NJ, Clayden J. Angew. Chem. Int. Ed. 2016; 55: 10755
- 2d Wang J, Chen M.-W, Ji Y, Hu S.-B, Zhou Y.-G. J. Am. Chem. Soc. 2016; 138: 10413
- 2e Mori K, Itakura T, Akiyama T. Angew. Chem. Int. Ed. 2016; 55: 11642
- 2f Yu C, Huang H, Li X, Zhang Y, Wang W. J. Am. Chem. Soc. 2016; 138: 6956
- 2g Fäseke VC, Sparr C. Angew. Chem. Int. Ed. 2016; 55: 7261
- 2h Moliterno M, Cari R, Puglisi A, Antenucci A, Sperandio C, Moretti E, Di Sabato A, Salvio R, Bella M. Angew. Chem. Int. Ed. 2016; 55: 6525
- 2i Gao H, Ess DH, Yousufuddin M, Kürti L. J. Am. Chem. Soc. 2013; 135: 7086
- 2j Chen Y.-H, Cheng D.-J, Zhang J, Wang Y, Liu X.-Y, Tan B. J. Am. Chem. Soc. 2015; 137: 15062
- 2k Zhang J.-W, Xu J.-H, Cheng D.-J, Shi C, Liu X.-Y, Tan B. Nat. Commun. 2016; 7: 10677
- 2l Link A, Sparr C. Angew. Chem. Int. Ed. 2014; 53: 5458
- 2m Barret KT, Metrano AJ, Rablen PR, Miller SJ. Nature 2014; 509: 71
- 2n Brandes S, Bella M, Kjoersgaard A, Jørgensen KA. Angew. Chem. Int. Ed. 2006; 45: 1147
- 2o Gustafson JL, Lim D, Miller SJ. Science 2010; 328: 1251
- 2p Li G.-Q, Gao H, Keene C, Devonas M, Ess DH, Kurti L. J. Am. Chem. Soc. 2013; 135: 7414
- 2q Mori K, Ichikawa Y, Kobayashi M, Shibata Y, Yamanaka M, Akiyama T. J. Am. Chem. Soc. 2013; 135: 3964
- 2r Armstrong RJ, Smith MD. Angew. Chem. Int. Ed. 2014; 53: 12822
- 2s Shirakawa S, Liu K, Maruoka K. J. Am. Chem. Soc. 2012; 134: 916
- 2t Hashimoto T, Sakata K, Tamakuni F, Dutton MJ, Maruoka K. Nat. Chem. 2013; 5: 240
- 3a Privileged Chiral Ligands and Catalysts . Zhou Q.-L. Wiley-VCH; Weinheim: 2011
- 3b Noyori R, Takaya H. Acc. Chem. Res. 1990; 23: 345
- 3c Kočovský P, Štěpán V, Smrčina M. Chem. Rev. 2003; 103: 3213
- 3d Berthod M, Mignani G, Woodward G, Lemaire M. Chem. Rev. 2005; 105: 1801
- 3e Akiyama T. Chem. Rev. 2007; 107: 5744
- 3f Bringmann G, Gulder T, Gulder TA. M, Breuning M. Chem. Rev. 2011; 111: 563
- 4a Curran DP, Qi H, Geib SJ, DeMello NC. J. Am. Chem. Soc. 1994; 116: 3131
- 4b Curran DP, Liu W, Chen CH.-T. J. Am. Chem. Soc. 1999; 121: 11012
- 4c Bruch A, Ambrosius A, Fröhlich R, Studer A, Guthrie DB, Zhang H, Curran DP. J. Am. Chem. Soc. 2010; 11452
- 4d Guthrie DB, Geib SJ, Curran DP. J. Am. Chem. Soc. 2011; 133: 115
- 4e Bruch A, Fröhlich R, Grimme S, Studer A, Curran DP. J. Am. Chem. Soc. 2011; 133: 16270
- 4f Guthrie DB, Geib SJ, Curran DP. J. Am. Chem. Soc. 2009; 131: 15492
- 5a Clayden J. Angew. Chem. Int. Ed. 1997; 36: 949
- 5b Dai W.-M, Yeung KK. Y, Wang Y. Tetrahedron 2004; 60: 4425
- 6a Clayden J. Chem. Commun. 2004; 127
- 6b Clayden J, Lai LW. Angew. Chem. Int. Ed. 1999; 38: 2556
- 6c Clayden J, Lund A, Vallverdú L, Helliwell M. Nature 2004; 431: 966
- 6d Clayden J, Lai LW, Helliwell M. Tetrahedron: Asymmetry 2001; 12: 695
- 7a Tanaka K, Takeishi K, Noguchi K. J. Am. Chem. Soc. 2006; 128: 4586
- 7b Kitagawa O, Takahashi M, Yoshikawa M, Taguchi T. J. Am. Chem. Soc. 2005; 127: 3676
- 7c Bennett DJ, Pickering PL, Simpkins NS. Chem. Commun. 2004; 1392
- 7d Duan W.-L, Imazaki Y, Shintani R, Hayashi T. Tetrahedron 2007; 63: 8529
- 7e Hughes AD, Price DA, Simpkins NS. J. Chem. Soc., Perkin Trans. 1 1999; 1295
- 7f Suda T, Noguchi K, Hirano M, Tanaka K. Chem. Eur. J. 2008; 14: 6593
- 7g Terauchi J, Curran DP. Tetrahedron: Asymmetry 2003; 14: 587
- 7h Kitagawa O, Kohriyama M, Taguchi T. J. Org. Chem. 2002; 67: 8682
- 7i Zhang J, Zhang Y, Lin L, Yao Q, Liu X, Feng X. Chem. Commun. 2015; 51: 10554
- 8a Di Iorio N, Righi P, Mazzanti A, Mancinelli M, Ciogli A, Bencivenni G. J. Am. Chem. Soc. 2014; 136: 10250
- 8b Eudier F, Righi P, Mazzanti A, Ciogli A, Bencivenni G. Org. Lett. 2015; 17: 1728
- 8c Di Iorio N, Champavert F, Erice A, Righi P, Mazzanti A, Bencivenni G. Tetrahedron 2016; 72: 5191
- 9 For an overview on the organocatalytic reactions of maleimides, see: Chauhan P, Kaur J, Chimni SS. Chem. Asian J. 2013; 8: 328
- 10a Liao Y.-H, Liu X.-L, Wu Z.-J, Cun L.-F, Zhang X.-M, Yuan W.-C. Org. Lett. 2010; 12: 2896
- 10b Li L, Chen W, Yang W, Pan Y, Liu H, Tan CH, Jiang Z. Chem. Commun. 2012; 48: 5124
- 10c Yang X, Wang C, Ni Q, Enders D. Synthesis 2012; 44: 2601
- 10d Shirakawa S, Makino H, Yoshidome T, Maruoka K. Tetrahedron 2014; 70: 7128
- 11a Crider AM, Kolczynski TM, Yates KM. J. Med. Chem. 1980; 23: 324
- 11b Curtin ML, Garland RB, Heyman HR, Frey RR, Michaelides MR, Li J, Pease LJ, Glaser KB, Marcotte PA, Davidsen SK. Bioorg. Med. Chem. Lett. 2002; 12: 2919
- 11c Isaka M, Rugseree N, Maithip P, Kongsaeree P, Prabpai S, Thebtaranonth Y. Tetrahedron 2005; 61: 5577
- 11d Uddin J, Ueda K, Siwu ER. O, Kita M, Uemura D. Bioorg. Med. Chem. 2006; 14: 6954
- 12a Dalpozzo R, Bartoli G, Bencivenni G. Chem. Soc. Rev. 2012; 41: 7247
- 12b Rottmann M, McNamara C, Yeung BK. S, Lee MC. S, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, González-Páez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck H.-P, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT. Science 2010; 329: 1175
- 12c Liu J.-J, Zhang Z (Hoffmann-La Roche AG) PCT Int. Appl WO 2008/055812, 2008
- 12d Ang SH, Krastel P, Leong SY, Tan LJ, Wong WL. J, Yeung BK. S, Zou B (Novartis AG) US Patent 2009/0275560 A1, 2009
- 12e Ding Q, Liu J.-J, Zhang Z. PCT Int. Appl WO 2007/104714, 2007
- 12f Vintonyak VV, Warburg K, Kruse H, Grimme S, Hübel K, Rauth D, Waldmann H. Angew. Chem. Int. Ed. 2010; 49: 5902
- 12g Claesson A, Swahn M.-M, Berge O.-G. US Patent 6,774,132, 2004
- 12h Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
- 12i Trost BM, Brennan MK. Synthesis 2009; 3003
- 12j Zhou F, Liu Y.-L, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
- 12k Quasdorf KW, Overman LE. Nature 2014; 516: 181
- 13a Alemán J, Parra A, Jiang H, Jørgensen KA. Chem. Eur. J. 2011; 17: 6890
- 13b Chauhan P, Mahajan S, Kaya U, Hack D, Enders D. Adv. Synth. Catal. 2015; 357: 253
- 13c Yu X, Wang W. Chem. Asian J. 2008; 3: 516
- 14 Under optimized conditions, the reaction of tert-butyl 3-(4-methoxybenzyl)-2-oxoindoline-1-carboxylate with maleimide 2a furnished a single diastereoisomer in 33% yield and 64% ee.
- 15 CCDC 1511895 contains the supplementary crystallographic data for compound 3p. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. See also Supporting Information for further details.
- 16 Aggarwal VK, Emma I, Fulford SY. J. Org. Chem. 2003; 68: 692
- 17 Still WC, Kahn M, Mitra AJ. J. Org. Chem. 1978; 43: 2923
- 18 Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M. J. Am. Chem. Soc. 2005; 127: 10164
- 19 Zhu X.-L, Xu J.-H, Cheng D.-J, Zhao L.-J, Liu X.-Y, Tan B. Org. Lett. 2014; 16: 2192
- 20a Neumann JJ, Rakshit S, Dröge T, Glorius F. Angew. Chem. Int. Ed. 2009; 48: 6892
- 20b Miller C, Hoyle C, Jönsson E. PCT WO 98/54134, 1998
- 21 Vakulya B, Varga S, Csámpai A, Soós T. Org. Lett. 2005; 7: 1967
- 22 Malerich JP, Hagihara K, Rawal VH. J. Am. Chem. Soc. 2008; 130: 14416
- 23 Lee JW, Ryu TH, Oh JS, Bae HY, Jang HB, Song CE. Chem. Commun. 2009; 7224
For reviews, see:
For selected research articles, see:
For comprehensive reviews, see: