SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 52, Issue 52, 2013, Pages 14143-14146

Enantioselective organocatalytic multicomponent synthesis of 2,6-diazabicyclo[2.2.2]octanones

(7) Sanchez Duque, Maria Del Mar a Baslé, Olivier a Génisson, Yves b Plaquevent, Jean Christophe b Bugaut, Xavier a Constantieux, Thierry a Rodriguez, Jean a

a AIX MARSEILLE UNIVERSITÉ (France)

b Université Paul Sabatier Toulouse III (France)

Author keywords

enantioselectivity; heterocycles; multicomponent reactions; organocatalysis; synthetic methods

Indexed keywords

CHEMOSELECTIVE REACTIONS; ENANTIOSELECTIVE; HETEROCYCLES; MULTI-COMPONENT REACTIONS; MULTICOMPONENT SYNTHESIS; ORGANOCATALYSIS; ORGANOCATALYTIC; SYNTHETIC METHODS;

CATALYSIS; MOLECULAR SIEVES; REACTION KINETICS; SCAFFOLDS;

ENANTIOSELECTIVITY;

EID: 84890593510 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201306656 Document Type: Article

Times cited : (35)

References (64)

1
- 84890597202
- Wiley-VCH, Weinheim
- J. Zhu, H. Bienaymé, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005
- (2005) Multicomponent Reactions
- Zhu, J.¹ Bienaymé, H.²

2
- 70349156384
- B. B. Touré, D. G. Hall, Chem. Rev. 2009, 109, 4439-4486
- (2009) Chem. Rev. , vol.109 , pp. 4439-4486
- Touré, B.B.¹ Hall, D.G.²

3
- 78349257436
- B. Jiang, T. Rajale, W. Wever, S.-J. Tu, G. Li, Chem. Asian J. 2010, 5, 2318-2335
- (2010) Chem. Asian J. , vol.5 , pp. 2318-2335
- Jiang, B.¹ Rajale, T.² Wever, W.³ Tu, S.-J.⁴ Li, G.⁵

4
- 84859223991
- E. Ruijter, R. Scheffelaar, R. V. A. Orru, Angew. Chem. 2011, 123, 6358-6371
- (2011) Angew. Chem. , vol.123 , pp. 6358-6371
- Ruijter, E.¹ Scheffelaar, R.² Orru, R.V.A.³

5
- 79959907066
- Angew. Chem. Int. Ed. 2011, 50, 6234-6246
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 6234-6246

6
- 84859359524
- M. J. Climent, A. Corma, S. Iborra, RSC Adv. 2012, 2, 16-58
- (2012) RSC Adv. , vol.2 , pp. 16-58
- Climent, M.J.¹ Corma, A.² Iborra, S.³

7
- 84862175237
- A. Dömling, W. Wang, K. Wang, Chem. Rev. 2012, 112, 3083-3135
- (2012) Chem. Rev. , vol.112 , pp. 3083-3135
- Dömling, A.¹ Wang, W.² Wang, K.³

8
- 84878639779
- S. Brauch, S. S. van Berkel, B. Westermann, Chem. Soc. Rev. 2013, 42, 4948-4962.
- (2013) Chem. Soc. Rev. , vol.42 , pp. 4948-4962
- Brauch, S.¹ Van Berkel, S.S.² Westermann, B.³

9
- 84873360342
- For a thorough discussion on this topic, see:, D. Bonne, T. Constantieux, Y. Coquerel, J. Rodriguez, Chem. Eur. J. 2013, 19, 2218-2231.
- (2013) Chem. Eur. J. , vol.19 , pp. 2218-2231
- Bonne, D.¹ Constantieux, T.² Coquerel, Y.³ Rodriguez, J.⁴

10
- 23044445558
- D. J. Ramõn, M. Yus, Angew. Chem. 2005, 117, 1628-1661
- (2005) Angew. Chem. , vol.117 , pp. 1628-1661
- Ramõn, D.J.¹ Yus, M.²

11
- 17144366282
- Angew. Chem. Int. Ed. 2005, 44, 1602-1634.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1602-1634

12
- 33745211429
- D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861-863.
- (2006) Nature , vol.441 , pp. 861-863
- Enders, D.¹ Hüttl, M.R.M.² Grondal, C.³ Raabe, G.⁴

13
- 34247172950
- G. Guillena, D. J. Ramõn, M. Yus, Tetrahedron: Asymmetry 2007, 18, 693-700
- (2007) Tetrahedron: Asymmetry , vol.18 , pp. 693-700
- Guillena, G.¹ Ramõn, D.J.² Yus, M.³

14
- 77649087999
- C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167-178
- (2010) Nat. Chem. , vol.2 , pp. 167-178
- Grondal, C.¹ Jeanty, M.² Enders, D.³

15
- 81255211335
- J. Yu, F. Shi, L.-Z. Gong, Acc. Chem. Res. 2011, 44, 1156-1171
- (2011) Acc. Chem. Res. , vol.44 , pp. 1156-1171
- Yu, J.¹ Shi, F.² Gong, L.-Z.³

16
- 84860478728
- C. de Graaff, E. Ruijter, R. V. A. Orru, Chem. Soc. Rev. 2012, 41, 3969-4009
- (2012) Chem. Soc. Rev. , vol.41 , pp. 3969-4009
- De Graaff, C.¹ Ruijter, E.² Orru, R.V.A.³

17
- 84868372172
- C. M. Marson, Chem. Soc. Rev. 2012, 41, 7712-7722.
- (2012) Chem. Soc. Rev. , vol.41 , pp. 7712-7722
- Marson, C.M.¹

18
- 11144310072
- C. Simon, T. Contantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957-4980
- (2004) Eur. J. Org. Chem. , pp. 4957-4980
- Simon, C.¹ Contantieux, T.² Rodriguez, J.³

19
- 33745775855
- F. Liéby-Muller, C. Simon, T. Constantieux, J. Rodriguez, QSAR Comb. Sci. 2006, 25, 432-438
- (2006) QSAR Comb. Sci. , vol.25 , pp. 432-438
- Liéby-Muller, F.¹ Simon, C.² Constantieux, T.³ Rodriguez, J.⁴

20
- 77956591638
- D. Bonne, Y. Coquerel, T. Constantieux, J. Rodriguez, Tetrahedron: Asymmetry 2010, 21, 1085-1109
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 1085-1109
- Bonne, D.¹ Coquerel, Y.² Constantieux, T.³ Rodriguez, J.⁴

21
- 84881341177
- X. Bugaut, D. Bonne, Y. Coquerel, J. Rodriguez, T. Constantieux, Curr. Org. Chem. 2013, 17, 1920-1928.
- (2013) Curr. Org. Chem. , vol.17 , pp. 1920-1928
- Bugaut, X.¹ Bonne, D.² Coquerel, Y.³ Rodriguez, J.⁴ Constantieux, T.⁵

22
- 29044446242
- F. Liéby-Muller, T. Constantieux, J. Rodriguez, J. Am. Chem. Soc. 2005, 127, 17176-17177.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 17176-17177
- Liéby-Muller, F.¹ Constantieux, T.² Rodriguez, J.³

23
- 72849149325
- To the best of our knowledge, there is only one report of a multiple bond-forming transformations with a 1,3-dicarbonyl resulting in the creation of more than five new bonds
- To the best of our knowledge, there is only one report of a multiple bond-forming transformations with a 1,3-dicarbonyl resulting in the creation of more than five new bonds:, M. Presset, Y. Coquerel, J. Rodriguez, Org. Lett. 2009, 11, 5706.
- (2009) Org. Lett. , vol.11 , pp. 5706
- Presset, M.¹ Coquerel, Y.² Rodriguez, J.³

24
- 80052337499
- Z. El Asri, Y. Génisson, F. Guillen, O. Baslé, N. Isambert, M. M. Sanchez Duque, S. Ladeira, J. Rodriguez, T. Constantieux, J.-C. Plaquevent, Green Chem. 2011, 13, 2549-2552.
- (2011) Green Chem. , vol.13 , pp. 2549-2552
- El Asri, Z.¹ Génisson, Y.² Guillen, F.³ Baslé, O.⁴ Isambert, N.⁵ Sanchez Duque, M.M.⁶ Ladeira, S.⁷ Rodriguez, J.⁸ Constantieux, T.⁹ Plaquevent, J.-C.¹⁰

25
- 0013144803
- N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685-689
- (2003) Angew. Chem. , vol.115 , pp. 685-689
- Halland, N.¹ Aburel, P.S.² Jørgensen, K.A.³

26
- 0037429423
- Angew. Chem. Int. Ed. 2003, 42, 661-665
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 661-665

27
- 2442629288
- M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 5672-5673
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5672-5673
- Bella, M.¹ Jørgensen, K.A.²

28
- 33750449772
- S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411-4415
- (2006) Angew. Chem. , vol.118 , pp. 4411-4415
- Brandau, S.¹ Landa, A.² Franzén, J.³ Marigo, M.⁴ Jørgensen, K.A.⁵

29
- 33746290813
- Angew. Chem. Int. Ed. 2006, 45, 4305-4309
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 4305-4309

30
- 55549133297
- J. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc. 2008, 130, 14416-14417; for a review, see
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14416-14417
- Malerich, J.P.¹ Hagihara, K.² Rawal, V.H.³

31
- 34250613134
- S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716.
- (2007) Eur. J. Org. Chem. , pp. 1701-1716
- Tsogoeva, S.B.¹

32
- 46149090587
- For a pseudo-three-component reaction initiated by an organocatalytic enantioselective Michael addition of a 1,3-dicarbonyl compound, see:, S. Bertelsen, R. L. Johansen, K. A. Jørgensen, Chem. Commun. 2008, 3016-3018
- (2008) Chem. Commun. , pp. 3016-3018
- Bertelsen, S.¹ Johansen, R.L.² Jørgensen, K.A.³

33
- 53249120666
- For a three-component reaction involving the addition to an in situ generated α,β-unsaturated imine, see:, J. Jiang, J. Yu, X.-X. Sun, Q.-Q. Rao, L.-Z. Gong, Angew. Chem. 2008, 120, 2492-2496
- (2008) Angew. Chem. , vol.120 , pp. 2492-2496
- Jiang, J.¹ Yu, J.² Sun, X.-X.³ Rao, Q.-Q.⁴ Gong, L.-Z.⁵

34
- 42449110313
- Angew. Chem. Int. Ed. 2008, 47, 2458-2462
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 2458-2462

35
- 67650286836
- For an enantioselective Hantzsch synthesis of polyhydroquinolines, see:, C. G. Evans, J. E. Gestwicki, Org. Lett. 2009, 11, 2957-2959
- (2009) Org. Lett. , vol.11 , pp. 2957-2959
- Evans, C.G.¹ Gestwicki, J.E.²

36
- 77149154764
- For a three-component reaction involving a conjugate addition to nitroolefins, see:, Y. Wang, R.-G. Han, Y.-L. Zhao, S. Yang, P.-F. Xu, D. J. Dixon, Angew. Chem. 2009, 121, 10018-10022
- (2009) Angew. Chem. , vol.121 , pp. 10018-10022
- Wang, Y.¹ Han, R.-G.² Zhao, Y.-L.³ Yang, S.⁴ Xu, P.-F.⁵ Dixon, D.J.⁶

37
- 72449151738
- Angew. Chem. Int. Ed. 2009, 48, 9834-9838.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9834-9838

38
- 0142072631
- T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 12672-12673
- Okino, T.¹ Hoashi, Y.² Takemoto, Y.³

39
- 11844302258
- T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119-125.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 119-125
- Okino, T.¹ Hoashi, Y.² Furukawa, T.³ Xu, X.⁴ Takemoto, Y.⁵

40
- 9244238796
- P. M. Pihko, Angew. Chem. 2004, 116, 2110-2113
- (2004) Angew. Chem. , vol.116 , pp. 2110-2113
- Pihko, P.M.¹

41
- 4544221552
- Angew. Chem. Int. Ed. 2004, 43, 2062-2064
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2062-2064

42
- 33746322013
- M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573
- (2006) Angew. Chem. , vol.118 , pp. 1550-1573
- Taylor, M.S.¹ Jacobsen, E.N.²

43
- 33646468489
- Angew. Chem. Int. Ed. 2006, 45, 1520-1543
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1520-1543

44
- 33746277515
- S. J. Connon, Chem. Eur. J. 2006, 12, 5418-5427
- (2006) Chem. Eur. J. , vol.12 , pp. 5418-5427
- Connon, S.J.¹

45
- 38349135345
- A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743
- (2007) Chem. Rev. , vol.107 , pp. 5713-5743
- Doyle, A.G.¹ Jacobsen, E.N.²

46
- 80055037232
- W.-Y. Siau, J. Wang, Catal. Sci. Technol. 2011, 1, 1298-1310.
- (2011) Catal. Sci. Technol. , vol.1 , pp. 1298-1310
- Siau, W.-Y.¹ Wang, J.²

47
- 33644619459
- H. Sundén, I. Ibrahem, L. Eriksson, A. Cõrdova, Angew. Chem. 2005, 117, 4955-4958
- (2005) Angew. Chem. , vol.117 , pp. 4955-4958
- Sundén, H.¹ Ibrahem, I.² Eriksson, L.³ Cõrdova, A.⁴

48
- 23744473863
- Angew. Chem. Int. Ed. 2005, 44, 4877-4880
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4877-4880

49
- 58649123793
- M. Bella, D. M. S. Schietroma, P. P. Cusella, T. Gasperi, V. Visca, Chem. Commun. 2009, 597-599
- (2009) Chem. Commun. , pp. 597-599
- Bella, M.¹ Schietroma, D.M.S.² Cusella, P.P.³ Gasperi, T.⁴ Visca, V.⁵

50
- 70349784950
- G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M.-P. Song, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7336-7339
- (2009) Angew. Chem. , vol.121 , pp. 7336-7339
- Bencivenni, G.¹ Wu, L.-Y.² Mazzanti, A.³ Giannichi, B.⁴ Pesciaioli, F.⁵ Song, M.-P.⁶ Bartoli, G.⁷ Melchiorre, P.⁸

51
- 70349784950
- Angew. Chem. Int. Ed. 2009, 48, 7200-7203
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7200-7203

52
- 81555226814
- D.-F. Yu, Y. Wang, P.-F. Xu, Adv. Synth. Catal. 2011, 353, 2960-2965
- (2011) Adv. Synth. Catal. , vol.353 , pp. 2960-2965
- Yu, D.-F.¹ Wang, Y.² Xu, P.-F.³

53
- 84862063769
- S. Abele, R. Inauen, D. Spielvogel, C. Moessner, J. Org. Chem. 2012, 77, 4765-4773.
- (2012) J. Org. Chem. , vol.77 , pp. 4765-4773
- Abele, S.¹ Inauen, R.² Spielvogel, D.³ Moessner, C.⁴

54
- 79959753211
- M. M. Sanchez Duque, O. Baslé, N. Isambert, A. Gaudel-Siri, Y. Génisson, J.-C. Plaquevent, J. Rodriguez, T. Constantieux, Org. Lett. 2011, 13, 3296-3299
- (2011) Org. Lett. , vol.13 , pp. 3296-3299
- Sanchez Duque, M.M.¹ Baslé, O.² Isambert, N.³ Gaudel-Siri, A.⁴ Génisson, Y.⁵ Plaquevent, J.-C.⁶ Rodriguez, J.⁷ Constantieux, T.⁸

55
- 84878775670
- W. Raimondi, M. M. Sanchez Duque, S. Goudedranche, A. Quintard, T. Constantieux, X. Bugaut, D. Bonne, J. Rodriguez, Synthesis 2013, 1659-1666.
- (2013) Synthesis , pp. 1659-1666
- Raimondi, W.¹ Sanchez Duque, M.M.² Goudedranche, S.³ Quintard, A.⁴ Constantieux, T.⁵ Bugaut, X.⁶ Bonne, D.⁷ Rodriguez, J.⁸

56
- 84890767871
- CCDC 951895 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
- CCDC 951895 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

57
- 33746877740
- Wiley-VCH, Weinheim
- J. Christoffers, A. Baro, Quaternary Stereocenters, Wiley-VCH, Weinheim, 2005
- (2005) Quaternary Stereocenters
- Christoffers, J.¹ Baro, A.²

58
- 27544458968
- J. Christoffers, A. Baro, Adv. Synth. Catal. 2005, 347, 1473
- (2005) Adv. Synth. Catal. , vol.347 , pp. 1473
- Christoffers, J.¹ Baro, A.²

59
- 32644439884
- B. M. Trost, C. Jiang, Synthesis 2006, 369
- (2006) Synthesis , pp. 369
- Trost, B.M.¹ Jiang, C.²

60
- 77957690100
- C. Hawner, A. Alexakis, Chem. Commun. 2010, 46, 7295; For a more specific review on the use of organocatalysis for that purpose, see
- (2010) Chem. Commun. , vol.46 , pp. 7295
- Hawner, C.¹ Alexakis, A.²

61
- 67650094837
- M. Bella, T. Gasperi, Synthesis 2009, 1583-1614.
- (2009) Synthesis , pp. 1583-1614
- Bella, M.¹ Gasperi, T.²

62
- 58149316209
- All the β-ketoamides bearing an electron-withdrawing group on the nitrogen atom were prepared according to our Wolff rearrangement methodology under microwave conditions:, M. Presset, Y. Coquerel, J. Rodriguez, J. Org. Chem. 2009, 74, 415-418.
- (2009) J. Org. Chem. , vol.74 , pp. 415-418
- Presset, M.¹ Coquerel, Y.² Rodriguez, J.³

63
- 84865431132
- For previous examples of iminium ion trapping with alkynyltrifluoroborates, see:, I. D. Jurberg, B. Peng, E. Wöstefeld, M. Wasserloos, N. Maulide, Angew. Chem. 2012, 124, 1986-1989
- (2012) Angew. Chem. , vol.124 , pp. 1986-1989
- Jurberg, I.D.¹ Peng, B.² Wöstefeld, E.³ Wasserloos, M.⁴ Maulide, N.⁵

64
- 84856873052
- Angew. Chem. Int. Ed. 2012, 51, 1950-1953.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1950-1953

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.