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-00000083.xml
Synlett 2015; 26(09): 1248-1252
DOI: 10.1055/s-0034-1380382
DOI: 10.1055/s-0034-1380382
letter
Asymmetric Conjugate Addition of Ketones to Maleimides Using Diaminomethyleneindenedione Organocatalyst
Further Information
Publication History
Received: 29 January 2015
Accepted after revision: 22 February 2015
Publication Date:
19 March 2015 (online)
Abstract
A novel diaminomethyleneindenedione (DMI) organocatalyst efficiently promotes the asymmetric conjugate addition of a ketone to a maleimide to afford the corresponding addition product in a high yield with up to 99% enantiomeric excess.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380382.
- Supporting Information
-
References and Notes
- 1 For reviews, see: Chauhan P, Kaur J, Chimni SS. Chem. Asian J. 2013; 8: 328
- 2a Fredenhagen A, Tamura SY, Kenny PT. M, Komura H, Naya Y, Nakanishi K, Nishiyama K, Sugiura M, Kita H. J. Am. Chem. Soc. 1987; 109: 4409
- 2b Malochet-Grivois C, Roussakis C, Robillard N, Biard JF, Riou D, Debitus C, Verbist JF. Anticancer Drug Des. 1992; 7: 493
- 2c Ando Y, Fuse E, Figg WD. Clin. Cancer Res. 2002; 8: 1964
- 2d Freiberg C, Brunner NA, Schiffer G, Lampe T, Pohlmann J, Brands M, Raabe M, Haebich D, Ziegelbauer K. J. Biol. Chem. 2004; 279: 26066
- 2e Isaka M, Rugseree N, Maithip P, Kongsaeree P, Prabpai S, Thebtaranonth Y. Tetrahedron 2005; 61: 5577
- 2f Uddin J, Ueda K, Siwu ER. O, Kita M, Uemura D. Bioorg. Med. Chem. 2006; 14: 6954
- 2g Aboul-Enein MN, El-Azzouny AA, Saleh OA, Maklad YA. Mini-Rev. Med. Chem. 2012; 12: 671
- 3 Bartoli G, Bosco M, Carlone A, Cavalli A, Locatelli M, Mazzanti A, Ricci P, Sambri L, Melchiorre P. Angew. Chem. Int. Ed. 2006; 45: 4966
- 4a Zhao G.-L, Xu Y, Sundén H, Eriksson L, Sayah M, Córdova A. Chem. Commun. 2007; 734
- 4b Xue F, Liu L, Zhang S, Duan W, Wang W. Chem. Eur. J. 2010; 16: 7979
- 4c Yu F, Jin Z, Huang H, Ye T, Liang X, Ye J. Org. Biomol. Chem. 2010; 8: 4767
- 4d Bai J.-F, Peng L, Wang L.-L, Wang L.-X, Xu X.-Y. Tetrahedron 2010; 66: 8928
- 4e Miura T, Masuda A, Ina M, Nakashima K, Nishida S, Tada N, Itoh A. Tetrahedron: Asymmetry 2011; 22: 1605
- 4f Ma Z.-W, Liu Y.-X, Li P.-L, Ren H, Zhu Y, Tao J.-C. Tetrahedron: Asymmetry 2011; 22: 1740
- 4g Miura T, Nishida S, Masuda A, Tada N, Itoh A. Tetrahedron Lett. 2011; 52: 4158
- 4h Ma Z.-W, Liu Y.-X, Zhang W.-J, Tao Y, Zhu Y, Tao J.-C, Tang M.-S. Eur. J. Org. Chem. 2011; 6747
- 4i Avila A, Chinchilla R, Nájera C. Tetrahedron: Asymmetry 2012; 23: 1625
- 4j Nugent TC, Sadiq A, Bibi A, Heine T, Zeonjuk LL, Vankova N, Bassil BS. Chem. Eur. J. 2012; 18: 4088
- 4k Yang W, Jiang K.-Z, Lu X, Yang H.-M, Li L, Lu Y, Xu L.-W. Chem. Asian J. 2013; 8: 1182
- 4l Durmaz M, Sirit A. Tetrahedron: Asymmetry 2013; 24: 1443
- 4m Avila A, Chinchilla R, Gómez-Bengoa E, Nájera C. Tetrahedron: Asymmetry 2013; 24: 1531
- 4n Kokotos CG. Org. Lett. 2013; 15: 2406
- 4o Qiao Y, Headley AD. Green Chem. 2013; 15: 2690
- 4p Orlandi S, Pozzi G, Ghisetti M, Benaglia M. New J. Chem. 2013; 37: 4140
- 4q Avila A, Chinchilla R, Gómez-Bengoa E, Nájera C. Eur. J. Org. Chem. 2013; 5085
- 4r Song Z.-T, Zhang T, Du H.-L, Ma Z.-W, Zhang C.-H, Tao J.-C. Chirality 2014; 26: 121
- 4s Flores-Ferrándiz J, Chinchilla R. Tetrahedron: Asymmetry 2014; 25: 1091
- 5a Yu F, Sun X, Jin Z, Wen S, Liang X, Ye J. Chem. Commun. 2010; 46: 4589
- 5b Wang J, Zhang M.-M, Zhang S, Xu Z.-A, Li H, Yu X.-H, Wang W. Synlett 2011; 473
- 5c Muramulla S, Ma J.-A, Zhao JC.-G. Adv. Synth. Catal. 2013; 355: 1260
- 6a Shen J, Nguyen TT, Goh Y.-P, Ye W, Fu X, Xu J, Tan C.-H. J. Am. Chem. Soc. 2006; 128: 13692
- 6b Zu L, Xie H, Li H, Wang J, Jiang W, Wang W. Adv. Synth. Catal. 2007; 349: 1882
- 6c Ye W, Jiang Z, Zhao Y, Goh SL. M, Leow D, Soh Y.-T, Tan C.-H. Adv. Synth. Catal. 2007; 349: 2454
- 6d Lu J, Zhou WJ, Liu F, Loh T.-P. Adv. Synth. Catal. 2008; 350: 1796
- 6e Jiang Z, Ye W, Yang Y, Tan C.-H. Adv. Synth. Catal. 2008; 350: 2345
- 6f Jiang Z, Pan Y, Zhao Y, Ma T, Lee R, Yang Y, Huang K.-W, Wong MW, Tan C.-H. Angew. Chem. Int. Ed. 2009; 48: 3627
- 6g Zea A, Valero G, Alba A.-NR, Moyano A, Rios R. Adv. Synth. Catal. 2010; 352: 1102
- 6h Liao Y.-H, Liu X.-L, Wu Z.-J, Cun L.-F, Zhang X.-M, Yuan W.-C. Org. Lett. 2010; 12: 2896
- 6i Alba A.-NR, Valero G, Calbet T, Font-Bard M, Moyano A, Rios R. Chem. Eur. J. 2010; 16: 9884
- 6j Wang J.-J, Dong X.-J, Wei W.-T, Yan M. Tetrahedron: Asymmetry 2011; 22: 690
- 6k Liao Y.-H, Liu X.-L, Wu Z.-J, Du X.-L, Zhang X.-M, Yuan W.-C. Adv. Synth. Catal. 2011; 353: 1720
- 6l Gómez-Torres E, Alonso DA, Gómez-Bengoa E, Nájera C. Org. Lett. 2011; 13: 6106
- 6m Shirakawa S, Terao SJ, He R, Maruoka K. Chem. Commun. 2011; 47: 10557
- 6n Ma Z.-W, Wu Y, Sun B, Du H.-L, Shi W.-M, Tao J.-C. Tetrahedron: Asymmetry 2013; 24: 7
- 6o Gómez-Torres E, Alonso DA, Gómez-Bengoa E, Nájera C. Eur. J. Org. Chem. 2013; 1434
- 6p Zhao M.-X, Ji F.-H, Wei D.-K, Shi M. Tetrahedron 2013; 69: 10763
- 7a Miyabe H, Takemoto Y. Bull. Chem. Soc. Jpn. 2008; 81: 785
- 7b Connon SJ. Chem. Commun. 2008; 2499
- 7c Connon SJ. Synlett 2009; 354
- 7d Takemoto Y. Chem. Pharm. Bull. 2010; 58: 593
- 7e Alemán J, Parra A, Jiang H, Jørgensen KA. Chem. Eur. J. 2011; 17: 6890
- 7f Bhadury PS, Li H. Synlett 2012; 23: 1108
- 7g Serdyuk OV, Heckel CM, Tsogoeva SB. Org. Biomol. Chem. 2013; 11: 7051
- 7h Tsakos M, Kokotos CG. Tetrahedron 2013; 69: 10199
- 8 Kanada Y, Yuasa H, Nakashima K, Murahashi M, Tada N, Itoh A, Koseki Y, Miura T. Tetrahedron Lett. 2013; 54: 4896
- 9 Hirashima S, Sakai T, Nakashima K, Watanabe N, Koseki Y, Mukai K, Kanada Y, Tada N, Itoh A, Miura T. Tetrahedron Lett. 2014; 55: 4334
- 10a Nakashima K, Hirashima S, Kawada M, Koseki Y, Tada N, Itoh A, Miura T. Tetrahedron Lett. 2014; 55: 2703
- 10b Nakashima K, Hirashima S, Akutsu H, Koseki Y, Tada N, Itoh A, Miura T. Tetrahedron Lett. 2015; 56: 558
- 11 Hirashima S, Nakashima K, Fujino Y, Arai R, Sakai T, Kawada M, Koseki Y, Murahashi M, Tada N, Itoh A, Miura T. Tetrahedron Lett. 2014; 55: 4619
- 12 Mashraqui SH, Hariharasubrahmanian H. J. Chem. Res., Synop. 1999; 492
- 13 Organocatalyst 3 Yellow powder; mp 179–180 °C; [α]D 29 –10.9 (c 1.00, CH2Cl2). 1H NMR (400 MHz, CDCl3): δ = 9.61 (br s, 1 H), 9.02 (d, J = 9.8 Hz, 1 H), 7.87 (s, 3 H), 7.61–7.57 (m, 2 H), 7.53–7.49 (m, 2 H), 5.13 (dd, J = 6.0, 16.3 Hz, 1 H) 4.88 (dd, J = 6.5, 16.3 Hz, 1 H), 3.15–3.06 (m, 1 H), 2.82–2.76 (m, 1 H), 1.89–0.87 (m, 10 H). 13C NMR (100 MHz, CDCl3): δ = 192.4, 161.5, 140.3, 138.6, 132.4 (q, 2 J C–F = 33.7 Hz), 132.3, 127.1, 123.1 (q, 1 J C–F = 273 Hz), 121.9, 120.5, 93.7, 61.3, 55.7, 47.7, 34.1, 33.2, 24.8, 24.2. Anal. Calcd for C25H23F6N3O2: C, 58.71; H, 4.53; N, 8.22. Found: C, 58.62; H, 4.52; N, 8.22.
- 14 Typical Procedure of the Conjugate Additions to Maleimides Using 3 To a mixture of N-phenylmaleimide (4a, 34.6 mg, 0.200 mmol) and acetone (73.4 μL, 1.00 mmol) in p-xylene (0.4 mL) was added organocatalyst 3 (20.5 mg, 0.040 mmol) and benzoic acid (2.5 mg, 0.020 mmol) at r.t. After stirring in closed tube at 40 °C for 48 h, the reaction mixture was directly purified by flash column chromatography on silica gel with a 3:2 to 1:1 mixture of hexane and EtOAc to afford 5a (37.3 mg, 81%) as a white powder.
For reviews, see: