An asymmetric Organocatalytic quadruple cascade to tetraaryl-substituted 2-azabicyclo[33.0]octadienones

Synthesis (Germany)

Volumn 46, Issue 11, 2014, Pages 1539-1546

  Joie, Céline ^a   Deckers, Kristina ^a   Raabe, Gerhard ^a   Enders, Dieter ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

aza Michael addition; domino reactions; organocatalysis; quadruple cascade; vinylogous Michael addition

Indexed keywords

ADDITION REACTIONS; CATALYSIS;

AZA-MICHAEL ADDITION; CASCADE PRODUCTS; DIASTEREOSELECTIVITIES; DOMINO REACTIONS; MICHAEL ADDITIONS; ORGANOCATALYSIS; ORGANOCATALYTIC; UNSATURATED ALDEHYDES;

REACTION KINETICS;

1 (3 CHLOROPHENYL) 2 OXO 3,6,6A TRIPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; 1 (4 METHOXYPHENYL) 2 OXO 3,6,6A TRIPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; 1 (4 NITROPHENYL) 2 OXO 3,6,6A TRIPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; 1 OXO 2,6A DIPHENYL 3,6 BIS[3,4,5 TRIS(BENZYLOXY)PHENYL] 1,2,6,6A TETRAHYDROCYCLOPENTA[C]PYRROLE 5 CARBALDEHYDE; 2 OXO 1,3,6,6A TETRAPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; 2 OXO 1,6,6A TRIPHENYL 3 (2 TOLYL) 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; 3 (4 CHLOROPHENYL) 2 OXO 1,6,6A TRIPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; 3,6 BIS(2 METHOXYPHENYL) 1 OXO 2,6A DIPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[C]PYRROLE 5 CARBALDEHYDE; 6,6A BIS(1,3 BENZODIOXOL 5 YL) 2 OXO 1,3 DIPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; 6,6A BIS(4 CHLOROPHENYL) 2 OXO 1,3 DIPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; 6,6A BIS(4 METHOXYPHENYL) 2 OXO 1,3 DIPHENYL 1,2,6,6A TETRAHYDROCYCLOPENTA[B]PYRROLE 5 CARBALDEHYDE; ALDEHYDE DERIVATIVE; AZABICYCLO DERIVATIVE; TERT BUTYL 3[4[1(TERT BUTOXYCARBONYL) 1H INDOL 2 YL] 5 FORMYL 3 OXO 2,3A DIPHENYL 2,3,3A,4 TETRAHYDROCYCLOPENTA[C]PYRROL 1 YL] 1H INDOLE 1 CARBOXYLATE; TETRAARYL 2 AZABICYCLO[3.3.0]OCTADIENONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; PROCESS DEVELOPMENT; PROCESS OPTIMIZATION; REACTION TIME; ROOM TEMPERATURE; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 84901635446     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1340982     Document Type: Article

References (84)

1. For selected reviews, see: a. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, 2005.
2. Dalko, P. I. Enantioselective Organocatalysis; Wiley-VCH: Weinheim, 2007.
3. Special issue List, B., Ed.): Chem. Rev. 2007, 107, 5413.
4. Vicario, J. L.; Badia, D.; Carillo, L. Synthesis 2007, 2065.
5. Tsogoeva S. B. Eur. J. Org. Chem. 2007, 1701.
6. de Figueiredo R. M.; Christmann M. Eur. J. Org. Chem. 2007, 2575.
7. Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638.
8. MacMillan, D. W. C. Nature London. 2008, 455, 304.
9. Barbas, C. F. III Angew. Chem. Int. Ed. 2008, 47, 42.
10. Enders, D.; Narine, A. A. J. Org. Chem. 2008, 73, 7857.
11. Jørgensen, K. A.; Bertelsen, S. Chem. Soc. Rev. 2009, 38, 2178.
12. Bella M.; Gasperi T. Synthesis 2009, 1583.
13. Merino, P.; Marquez-Lopez, E.; Tejero, T.; Herrera, R. P. Synthesis 2010, 1.
14. Marcelli, T.; Hiemstra, H. Synthesis 2010, 1229.
15. Terada, M. Synthesis 2010, 1929.
16. Pellissier, H. Recent Developments in Asymmetric Organocatalysis; RSC: Cambridge, 2010.
17. Ramachary D. B.; Jain S. Org. Biomol. Chem. 2011, 9, 1277.
18. Moyano, A.; Rios, R. Chem. Rev. 2011, 111, 4703.
19. Pellissier, H. Tetrahedron 2012, 68, 2197.
20. Maruoka K.; List B.; Yamamoto H.; Gong L.-Z. Chem. Commun. 2012, 48, 10703.
21. List, B.; Maruoka, K. Asymmetric Organocatalysis, In Science of Synthesis; Thieme: Stuttgart, 2012.
22. Scheffler U.; Mahrwald R. Chem. Eur. J. 2013, 19, 14346.
23. Selig, P. Synthesis 2013, 45, 703.
24. Dalko, P. I. Comprehensive Enantioselective Organocatalysis: Catalysts Reactions and Applications; Wiley-VCH: Weinheim, 2013.
25. For selected reviews on organocatalytic domino reactions, see: Volla, C. M. R.; Atodiresei, I.; Rueping, M. Chem. Rev. 2014, 114, 2390.
26. Goudedranche, S.; Raimondi, W.; Bugaut, X.; Constantieux, T.; Bonne, D.; Rodriguez, J. Synthesis 2013, 45, 1909.
27. Lu L.-Q.; Chen J.-R.; Xiao W.-J. Acc. Chem. Res. 2012, 45, 1278.
28. Pellissier H. Adv. Synth. Catal. 2012, 354, 237.
29. Enders, D.; Grossmann, A. Angew. Chem. Int. Ed. 2012, 51, 314.
30. Jørgensen, K. A.; Albrecht, Ł.; Jiang, H. Angew. Chem. Int. Ed. 2011, 50, 8492.
31. Grondal, C.; Jeanty, M.; Enders, D. Nature Chem. 2010, 2, 167.
32. Alba A.-N.; Companyo X.; Viciano M.; Rios R. Curr. Org. Chem. 2009, 13, 1432.
33. Yu X.; Wang W. Org. Biomol. Chem. 2008, 6, 2037.
34. Enders, D.; Grondal, C.; Hüttl, M. R. H. Angew. Chem. Int. Ed. 2007, 46, 1570.
35. For selected reviews on amine catalysis, see: Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem. Int. Ed. 2008, 47, 6138.
36. Nielsen M.; Worgull D.; Zweifel T.; Gschwend B.; Bertelsen S.; Jørgensen K. A. Chem. Commun. 2011, 47, 632.
37. Sunoj, R. B. WIREs Comput. Mol. Sci. 2011, 1, 920.
38. Jensen, K. L.; Dickmeiss, G.; Jiang, H.; Albrecht, Ł.; Jørgensen, K. A. Acc. Chem. Res. 2012, 45, 248.
39. For examples of asymmetric secondary-amine-catalyzed simple domino reactions, see: Alexakis, A.; Lefranc, A.; Guénée, L. Org. Lett. 2013, 15, 2172.
40. Lee H.-J.; Cho C.-W. Eur. J. Org. Chem. 2013 387.
41. Wu, L.; Wang, Y.; Song, H.; Tang, L.; Zhou, Z.; Tang, C. Chem. Asian J. 2013, 8, 2204.
42. Zhang, X.; Song, X.; Li, H.; Zhang, S.; Chen, X.; Yu, X.; Wang, W. Angew. Chem. Int. Ed. 2012, 51, 7282.
43. Wang, C.; Yang, X.; Raabe, G.; Enders, D. Adv. Synth. Catal. 2012, 354, 2629.
44. Rueping, M.; Kuenkel, A.; Tato, F.; Bats, J. W. Angew. Chem. Int. Ed. 2009, 48, 3699.
45. Enders, D.; Wang, C.; Raabe, G. Synthesis 2009, 4119.
46. Li, H.; Zu, L.; Xie, H.; Wang, J.; Wang, W. Chem. Commun. 2008, 5636.
47. Wang W.; Li H.; Wang J.; Zu L. J. Am. Chem. Soc. 2006, 128, 10354.
48. Bui, T.; Barbas, C. F. III Tetrahedron Lett. 2000, 41, 6951.
49. For examples of asymmetric secondary amine catalyzed triple domino reactions, see: Dong, L.-J.; Fan, T.-T.; Wang, C.; Sun, J. Org. Lett. 2013, 15, 204.
50. Enders D.; Joie C.; Deckers K. Chem. Eur. J. 2013, 19, 10818.
51. Chatterjee, I.; Bastida, D.; Melchiorre, P. Adv. Synth. Catal. 2013, 355, 3124.
52. Jiang K.; Jia Z. J.; Chen S.; Wu L.; Chen Y. C. Chem. Eur. J. 2010, 16, 2852.
53. Urushima, T.; Sakamoto, D.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2010, 12, 4588.
54. Bencivenni, G.; Wu, L. Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M. P.; Bartoli, G.; Melchiorre, P. Angew. Chem. Int. Ed. 2009, 48, 7200.
55. Enders D.; Hüttl M. R. M.; Raabe G.; Bats J. W. Adv. Synth. Catal. 2008, 350, 267.
56. Carlone, A.; Cabrera, S.; Marigo, M.; Jorgensen, K. A. Angew. Chem. Int. Ed. 2007, 46, 1101.
57. Enders, D.; Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature (London) 2006, 441, 861.
58. For examples of asymmetric secondary amine catalyzed quadruple domino reactions, see: Zeng, X.; Ni, Q.; Raabe, G.; Enders, D. Angew. Chem. Int. Ed. 2013, 52, 2977.
59. Erdmann, N.; Philipps, A. R.; Atodiresei, I.; Enders, D. Adv. Synth. Catal. 2013, 355, 847.
60. Enders D.; Greb A.; Deckers K.; Selig P.; Merkens C. Chem. Eur. J. 2012, 18, 10226.
61. Rueping M.; Haack K.; Ieasuwan W.; Sundén H.; Blanco M.; Shoepke F. R. Chem. Commun. 2011, 47, 3828.
62. Krüll, R.; Bettray, W.; Enders, D. Synthesis 2010
63. Wang, C.; Mukanova, M.; Greb, A.; Enders, D. Chem. Commun. 2010, 46, 2477.
64. Jiang K.; Jia Z.-J.; Yin X.; Wu L.; Chen Y. C. Org. Lett. 2010, 12, 2766.
65. Hong, B.-C.; Kotame, P.; Tsai, C.-W.; Liao, J.-H. Org. Lett. 2010, 12, 776.
66. Zhang, F.-L.; Xu, A.-W.; Gong, Y.- F.; Wei, M.-H.; Yang, X.-L. Chem. Eur. J. 2009, 15, 6815.
67. Kotame, P.; Hong, B.-C.; Liao, J.-H. Tetrahedron Lett. 2009, 50, 704.
68. Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. Chem. Rev. 2011, 111, 3076; and references therein.
69. Curti, C.; Rassu, G.; Zambrano, V.; Pinna, L.; Pelosi, G.; Sartori, A.; Battistini, L.; Zanardi, F.; Casiraghi, G. Angew. Chem. Int. Ed. 2012, 51, 6200.
70. Manna S.; Kumar V.; Mukherjee S. Chem. Commun. 2012, 48, 5193.
71. Manna, S.; Mukherjee, S. Chem. Eur. J. 2012, 18, 15277.
72. Zhu, X.-L.; He, W.-J.; Yu, L.-L.; Cai, C.-W.; Zuo, Z.-L.; Qin, D.-B.; Liu, Q.-Z.; Jing, L.-H. Adv. Synth. Catal. 2012, 354, 2965.
73. Xu J.; Jin Z.; Chi Y. R. Org. Lett. 2013, 15, 5028.
74. Das U.; Chen Y. R.; Tsai Y. L.; Lin W. Chem. Eur. J. 2013, 19, 7713.
75. Rassu G.; Zambrano V.; Pinna L.; Curti C.; Battistini L.; Sartori A.; Pelosi G.; Zanardi F.; Casiraghi G. Adv. Synth. Catal., 2013, 355, 1881
76. Tanabe, H.; Xu, Y.; Sun, B.; Matsunaga, S.; Shibasaki, M. Heterocycles 2006, 86, 611.
77. Shepherd N. E.; Tanabe H.; Xu Y. Matsunaga S. Shibasaki M. J. Am. Chem. Soc., 2010, 132, 3666.
78. Feng X.; Cui H. L.; Xu S.; Wu L.; Chen Y. C. Chem. Eur. J. 2010, 16, 10309.
79. Choudhury A. R.; Mukherjee S. Org. Biomol. Chem. 2012, 10, 7313.
80. For reviews on organocatalytic asymmetric aza-Michael reactions, see: Kwong, F. Y.; Wang, J.; Li, P.; Choy, P. Y.; Chan, A. S. C. ChemCatChem 2012, 4, 917.
81. Enders D.; Wang C.; Liebich J. X. Chem. Eur. J. 2009, 15, 11058.
82. Krishna, P. R.; Sreeshailam, A.; Srinivas, R. Tetrahedron 2009, 65, 9657.
83. Joie, C.; Deckers, K.; Enders, D. Synthesis 2014, 46, 799.
84. CCDC 984016 4a. and CCDC 986325 ent-10a. contain 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.