Novel tetrahydroisoquinoline based organocatalysts for asymmetric Diels-Alder reactions: Insight into the catalytic mode using ROESY NMR and DFT studies

Tetrahedron Asymmetry

Volumn 21, Issue 23, 2010, Pages 2859-2867

  Naicker, Tricia ^a   Petzold, Katja ^a   Singh, Thishana ^b   Arvidsson, Per I ^a,c,d   Kruger, Hendrik G ^a   Maguire, Glenn E M ^a   Govender, Thavendran ^a  

^a UNIVERSITY OF KWAZULU NATAL   (South Africa)

^b DURBAN UNIVERSITY OF TECHNOLOGY   (South Africa)

^c UPPSALA UNIVERSITY   (Sweden)

^d ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

6,7 DIMETHOXY 1 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; ALKADIENE; CINNAMALDEHYDE; CYCLOHEXANE; TETRAHYDROISOQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CATALYST SUPPORT; CORRELATION ANALYSIS; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 78651391497     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.11.010     Document Type: Article

References (51)

1. P.I. Dalko, Enantioselective Organocatalysis 2007 Wiley-VCH Verlag Gmb & Co KGaA Weinheim
2. A. Dondoni, and A. Massi Angew. Chem., Int. Ed. 47 2008 4638 4660
3. P. Melchiorre, M. Marigo, A. Carlone, and G. Bartoli Angew. Chem., Int. Ed. 47 2008 6138 6171
4. A. Erkkila, I. Majander, and P.M. Pihko Chem. Rev. 107 2007 5416 5470
5. G. Lelais, and D.W.C. MacMillan Aldrichim. Acta 39 2006 79 87
6. B. List Chem. Commun. 2006 819 824
7. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471 5569
8. K.A. Ahrendt, C.J. Borths, and D.W.C. MacMillan J. Am. Chem. Soc. 122 2000 4243 4244
9. J. Franzen, M. Marigo, D. Fielenbach, T.C. Wabnitz, A. Kjaersgaard, and K.A. Jorgensen J. Am. Chem. Soc. 127 2005 18296 18304
10. B. List, R.A. Lerner, and C.F. Barbas J. Am. Chem. Soc. 122 2000 2395 2396
11. Z.-Z. Liu, Y. Wang, Y.-F. Tang, S.-Z. Chen, X.-G. Chen, and H.-Y. Li Bioorg. Med. Chem. Lett. 16 2006 1282 1285
12. J.D. Scott, and R.M. Williams Chem. Rev. 102 2002 1669 1730
13. J.E. Tarver, A.J. Pfizenmayer, and M.M. Joullié J. Org. Chem. 66 2001 7575 7587
14. M.E. Zarranz De Ysern, and L.A. Ordoñez Prog. Neuro- Psychopharmacol. 5 1981 343 355
15. P.I. Arvidsson, T. Govender, H.G. Kruger, G.E.M. Maguire, and T. Naicker S. Afr. J. Chem. 62 2009 60 66
16. G.A. Boyle, T. Govender, H.G. Kruger, and G.E.M. Maguire Tetrahedron: Asymmetry 15 2004 3775 3781
17. G.A. Boyle, T. Govender, H.G. Kruger, and G.E.M. Maguire Tetrahedron: Asymmetry 15 2004 2661 2666
18. D. Basavaiah, U. Das, and S. Roy J. Chem. Sci. 121 2009 1003 1010
19. C. Blanc, J. Hannedouche, and F. Agbossou-Niedercorn Tetrahedron Lett. 44 2003 6469 6473
20. Y. Hari, M. Sakuma, A. Miyakawa, K. Hatano, and T. Aoyama Heteroycles 2008 305 311
21. K. Stingl, J. Martens, and S. Wallbaum Tetrahedron: Asymmetry 3 1992 223 226
22. S.K. Chakka, P.G. Andersson, G.E.M. Maguire, H.G. Kruger, and T. Govender Eur. J. Org. Chem. 2010 972 980
23. B.K. Peters, S.K. Chakka, T. Naicker, G.E.M. Maguire, H.G. Kruger, P.G. Andersson, and T. Govender Tetrahedron: Asymmetry 21 2010 679 687
24. R.B. Kawthekar, S.K. Chakka, V. Francis, P.G. Andersson, H.G. Kruger, G.E.M. Maguire, and T. Govender Tetrahedron: Asymmetry 21 2010 846 852
25. S.K. Chakka, B.K. Peters, G.E.M. Maguire, H.G. Kruger, P.G. Andersson, and T. Govender Tetrahedron: Asymmetry 2010
26. B. List Synth. Lett. 2001 1675 1686
27. G.L. Grunewald, D.J. Sall, and J.A. Monn J. Med. Chem. 31 1988 824 830
28. S. Aubry, S. Pellet-Rostaing, R. Faure, and M. Lemaire J. Heterocycl. Chem. 43 2006 139 148
29. T.B. Cai, A. Zou, J.B. Thomas, L. Brieaddy, H.A. Navarro, and F.I. Carrol J. Med. Chem. 2008 1849 1860
30. Y.F. Tang, Z.Z. Liu, and S.Z. Chen Tetrahedron Lett. 44 2003 7091 7094
31. C. Palomo, and A. Mielgo Angew. Chem., Int. Ed. 45 2006 7876 7880
32. V.K. Aggarwal, F. Sandrinelli, and J.P.H. Charmant Tetrahedron: Asymmetry 13 2002 87 93
33. A. Hartikka, L. Hojabri, P.P. Bose, and P.I. Arvidsson Tetrahedron: Asymmetry 20 2009 1871 1876
34. M. Lemay, and W.W. Ogilvie Org. Lett. 7 2005 4141 4144
35. U. Groselj, W.B. Schweizer, M.-O. Ebert, and D. Seebach Helv. Chim. Acta 92 2009 1 13
36. U. Groselj, D. Seebach, D.M. Badine, W.B. Schweizer, A.K. Beck, I. Krossing, P. Klose, Y. Hayashi, and T. Uchimaru Helv. Chim. Acta 92 2009 1225 1259
37. D. Seebach, R. Gilmour, U. Groselj, G. Deniau, C. Sparr, M.-O. Ebert, A.K. Beck, L.B. McCusker, D. Sisak, and T. Uchimaru Helv. Chim. Acta 93 2010 603 634
38. D. Seebach, U. Groselj, D.M. Badine, W.B. Schweizer, and A.K. Beck Helv. Chim. Acta 91 2008 1999 2034
39. T. Naicker, T. Govender, H.G. Kruger, and G.E.M. Maguire Acta Crystallogr., Sect. E: Struct. Rep. 66 2010 0638
40. T. Naicker, M. McKay, T. Govender, H.G. Kruger, and G.E.M. Maguire Acta Crystallogr., Sect. E: Struct. Rep. 65 2009 o3278
41. R. Gordillo, and K.N. Houk J. Am. Chem. Soc. 128 2006 3543 3553
42. T. Kano, Y. Tanaka, and K. Maruoka Org. Lett. 8 2006 2687 2689
43. H. Gotoh, and Y. Hayashi Org. Lett. 9 2007 2859 2862
44. H. He, B.J. Pei, H. Chou, T. Tian, W.H. Cha, and A.W.M. Lee Org. Lett. 10 2008 2421 2424
45. C.M. Thiele, K. Petzold, and J. Schleucher Chem. Eur. J. 15 2009 585 588
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A.F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. gaussian 09 Revision A. 1; Gaussian, Inc.: Wallingford CT, 2009.
47. A.D. Becke J. Chem. Phys. 97 1992 9173 9177
48. A.D. Becke J. Chem. Phys. 96 1992 2155 2160
49. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
50. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
51. J.J.P. Stewart J. Mol. Model. 13 2007 1173 1213