Chiral pyrrolidine-azole conjugates: Simple and efficient asymmetric organocatalysts for Michael addition to nitrostyrenes

Chinese Science Bulletin

Volumn 55, Issue 17, 2010, Pages 1735-1741

  Zhang, Long ^a   Xu, Hui ^b   Mi, Xue Ling ^a   Luo, San Zhong ^b   Cheng, Jin Pei ^a,b  

^a NANKAI UNIVERSITY   (China)

^b INSTITUTE OF CHEMISTRY   (China)

Author keywords

Azole; Michael addition; Nitrostyrene; Organocatalysis; Pyrrolidine

Indexed keywords

EID: 77953881545     PISSN: 10016538     EISSN: 18619541     Source Type: Journal    
DOI: 10.1007/s11434-010-3120-9     Document Type: Article

References (61)

1. Berner O M, Tedeschi L, Enders D. Asymmetric Michael addition to nitroalkenes. Eur J Org Chem, 2002, 12: 1877-1894.
2. Tsogoeva S B. Recent advances in asymmetric organocatalytic 1, 4-conjugate additions. Eur J Org Chem, 2007, 11: 1701-1716.
3. List B, Pojarliev P, Martin H J. Efficient proline-catalyzed Michael additions of unmodified ketones to nitroolefins. Org Lett, 2001, 3: 2423-2425.
4. Tsogoeva S B, Wei S W. Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea-amine bifunctional organocatalysts. Chem Commun, 2006, 1451-1453.
5. Huang H B, Jacobsen E N. Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst. J Am Chem Soc, 2006, 128: 7170-7171.
6. Lalonde M P, Chen Y G, Jacobsen E N. A chiral primary amine thiourea catalyst for the highly enantioselective direct conjugate addition of α,α-disubstituted aldehydes to nitroalkenes. Angew Chem Int Ed, 2006, 45: 6366-6370.
7. Xu Y M, Córdova A. Simple highly modular acyclic amine-catalyzed direct enantioselective addition of ketones to nitro-olefins. Chem Commun, 2006, 460-462.
8. Xu Y M, Zou W B, Sundén H, et al. Small peptide-catalyzed enantioselective addition of ketones to nitroolefins. Adv Synth Catal, 2006, 249: 418-424.
9. McCooey S H, Connon S J. Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins. Org Lett, 2007, 4: 599-602.
10. Liu K, Cui H F, Nie J, et al. Highly enantioselective michael addition of aromatic ketones to nitroolefins promoted by chiral bifunctional primary amine-thiourea catalysts based on saccharides. Org Lett, 2007, 5: 923-925.
11. Xue F, Zhang S L, Duan W H, et al. A novel bifunctional sulfonamide primary amine-catalyzed enantioselective conjugate addition of ketones to nitroolefins. Adv Synth Catal, 2008, 350: 2194-2198.
12. Cobb A J A, Longbottomv D A, Shaw D M, et al. 5-pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nirto-olefins. Chem Commun, 2004, 1808-1809.
13. Cobb A J A, Shaw D M, Longbottom D A, et al. Orgnocatalysis with proline derivatives: Improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions. Org Biomol Chem, 2005, 3: 84-96.
14. Betancort J M, Barbas C F III. Catalytic direct asymmetric michael reactions: Taming naked aldehyde donors. Org Lett, 2001, 23: 3737-3740.
15. Mase N, Thayumanavan R, Tanaka F, et al. Direct asymmetric organocatalytic michael reactions of α,α-disubstituted aldehydes with β-nitrostyrenes for the synthesis of quaternary carbon-containing products. Org Lett, 2004, 15: 2527-2530.
16. Pansare S V, Pandya K. Simple diamine- and triamine-protonic acid catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes. J Am Chem Soc, 2006, 128: 9624-9625.
17. Mase N, Watanabe K, Yoda H, et al. Organocatalytic direct Michael reaction of ketones and aldehydes with-nitrostyrene in brine. J Am Chem Soc, 2006, 128: 4966-4967.
18. Vishnumaya Singh V K. Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins. Org Lett, 2007, 6: 1117-1119.
19. Alexakis A, Andrey O. Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene. Org Lett, 2002, 21: 3611-3614.
20. Andrey O, Vidonne A, Alexakis A. Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin. Tetrahedron Lett, 2003, 44: 7901-7904.
21. Andrey O, Alexakis A, Bernardinelli G. Asymmetric Michael addition of -hydroxyketones to nitroolefins catalyzed by chiral diamine. Org Lett, 2003, 14: 2559-2561.
22. Andrey O, Alexakis A, Tomassini A, et al. The use of N-alkyl-2, 2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins. Adv Synth Catal, 2004, 346: 1147-1168.
23. Zhu M K, Cun L F, Mi A Q, et al. A highly enantioselective organocatalyst for the Michael addition of cyclic ketones to nitroolefins. Tetrahedron: Asymmetry, 2006, 17: 491-493.
24. Chen H B, Wang Y, Wei S Y, et al. L-proline derived triamine as a highly stereoselective organocatalyst for asymmetric Michael addition of cyclohexanone to nitroolefins. Tetrahedron: Asymmetry, 2007, 18: 1308-1312.
25. Mossé S, Laars M, Kriis K, et al. 3, 3′-bimorpholine derivatives as a new class of organocatalysts for asymmetric Michael addition. Org Lett, 2006, 12: 2559-2562.
26. Barros M T, Phillips A M F. Chiral piperazines as efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes. Eur J Org Chem, 2007, 1: 178-185.
27. Ishii T, Fujioka S, Sekiguchi Y, et al. A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions. J Am Chem Soc, 2004, 126: 9558-9559.
28. Wang W, Wang J, Li H. Direct, highly enantioselective pyrrolidine sulfonamide catalyzed Michael addition of adlehydes to Nitrostyrenes. Angew Chem Int Ed, 2005, 44: 1369-1371.
29. Zu L S, Wang J, Li H, et al. A recyclable Fluorous (s)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water. Org Lett, 2006, 14: 3077-3079.
30. Wang J, Li H, Lou B, et al. Enantio- and Diastereoselective Michael addition reactions of unmodified aldehydes and ketones with nitroolefins catalyzed by a pyrrolidine sulfonamide. Chem Eur J, 2006, 12: 4321-4332.
31. Diez D, Gil M J, Moro R F, et al. A new class of chiral pyrrolidine for asymmetric Michael addition reactions. New mechanism via simple 4+2 type attack of the enamine on the trans-nitrostyrene. Tetrahedron, 2007, 63: 740-747.
32. Cao C L, Ye M C, Sun X L, et al. Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins. Org Lett, 2006, 14: 2901-2904.
33. Cao Y J, Lai Y Y, Wang X, et al. Michael additions in water of ketones to nitroolefins catalyzed by readily tunable and bifunctional pyrrolidine-thiourea organocatalysts. Tetrahedron Lett, 2007, 48: 21-24.
34. Hayashi Y, Gotoh H, Hayashi T, et al. Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes. Angew Chem Int Ed, 2005, 44: 4212-4215.
35. Zu L S, Li H, Wang J, et al. Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether. Tetrahedron Lett, 2006, 47: 5131-5134.
36. Li Y W, Liu X Y, Zhao G. Effective and recyclable dendritic catalysts for the direct asymmetric Michael addition of aldehydes to nitrostyrenes. Tetrahedron: Asymmetry, 2006, 17: 2034-2039.
37. Albertshofer K, Thayumanavan R, Utsumi N, et al. Amine-catalyzed Michael reactions of an aminoaldehyde derivative to nitroolefins. Tetrahedron Lett, 2007, 48: 693-696.
38. Zhu S L, Yu S Y, Ma D W. Highly efficient catalytic system for enantioselective Michael addition of aldehydes to nitroalkenes in water. Angew Chem Int Ed, 2008, 47: 545-548.
39. García-García P, Ladépêche A, Halder R, et al. Catalytic asymmetric Michael reactions of acetaldehyde. Angew Chem Int Ed, 2008, 47: 4719-4721.
40. Hayashi Y, Itoh T, Ohkubo M, et al. Asymmetric Michael reaction of acetaldehyde catalyzed by diphenylprolinol silyl ether. Angew Chem Int Ed, 2008, 47: 4722-4724.
41. Palomo C, Vera S, Mielgo A, et al. Highly efficient asymmetric Michael addition of aldehydes to nitroalkenes catalyzed by a simple trans-4-hydroxyprolylamide. Angew Chem Int Ed, 2006, 45: 5984-5987.
42. Wang C, Yu C, Liu C L, et al. 4-Trifluoromethanesulfonamidyl prolinol tert-butyldiphenylsilyl ether as a highly efficient bifunctional organocatalyst for Michael addition of ketones and aldehydes to nitroolefins. Tetrahedron Lett, 2009, 50: 2363-2366.
43. Luo S Z, Mi X L, Zhang L, et al. Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to Nitroolefins. Angew Chem Int Ed, 2006, 45: 3093-3097.
44. Luo S Z, Mi X L, Liu S, et al. Surfactant-type asymmetric organocatalyst: Organocatalytic asymmetric Michael addition to nitrostyrenes in water. Chem Commun, 2006, 3687-3689.
45. Luo S Z, Zhang L, Mi X L, et al. Functionalized chiral ionic liquid catalyzed enantioselective desymmetrizations of prochiral ketones via asymmetric Michael addition reaction. J Org Chem, 2007, 24: 9350-9352.
46. Luo S Z, Xu H, Mi X L, et al. Evolution of pyrrolidine-type asymmetric organocatalysts by "click" chemistry. J Org Chem, 2006, 24: 9244-9247.
47. Yan Z Y, Niu Y N, Wei H L, et al. Combining proline and 'click chemistry': A class of versatile organocatalysts for the highly diastereo- and enantioselective michael addition in water. Tetrahedron: Asymmetry, 2006, 17: 3288-3293.
48. Almasi D, Alonso D A, Nájera C. Enantioselective conjugate addition of ketones to -nitrostyrenes catalyzed by 1, 2-amino alcoholde-rived prolinamides. Tetrahedron: Asymmetry, 2006, 17: 2064-2068.
49. Reyes E, Vicario J L, Badia D, et al. Organocatalytic asymmetric Michael addition of aldehydes to -nitroacroleine dimethyl acetal. Org Lett, 2006, 26: 6135-6138.
50. Clarke M L, Fuentes J A. Self-assembly of organocatalysts: Fine-tuning organocatalytic reactions. Angew Chem Int Ed, 2007, 46: 930-933.
51. Li P H, Wang L, Wang M, et al. Polymer-immobilized pyrrolidine-based chiral ionic liquids as recyclable organocatalysts for asymmetric Michael additions to Nitrostyrenes under solvent-free reaction conditions. Eur J Org Chem, 2008, 7: 1157-1160.
52. Li P H, Wang L, Zhang Y C, et al. Silica gel supported pyrrolidine-based chiral ionic liquid as recyclable organocatalyst for asymmetric Michael addition to nitrostyrenes. Tetrahedron, 2008, 64: 7633-7638.
53. Mandal T, Zhao C G. Modularly designed organocatalytic assemblies for direct nitro-Michael addition reactions. Angew Chem Int Ed, 2008, 47: 7714-7717.
54. Xu D Q, Luo S P, Wang L F, et al. Organoctalysts wrapped around by poly(ethylene glycol)s (PEGs): A unique host-guest system for asymmetric Michael addition reactions. Chem Commun, 2007, 4393- 4395.
55. Xu D Q, Wang B T, Luo S P, et al. Pyrrolidine-pyridinium based organocatalysts for highly enantioselective Michael addition of cyclohexanone to nitroalkenes. Tetrahedron: Asymmetry, 2007, 18: 1788-1794.
56. Xu D Q, Wang L P, Luo S P, et al. 2-[(Imidazolylthio)methyl]pyrrolidine as a trifunctional organocatalyst for the highly asymmetric michael addition of ketones to nitroolefins. Eur J Org Chem, 2008, 1049-1053.
57. Ni B K, Zhang Q Y, Headley A D. Pyrrolildine-based chiral pyridinium ionic liquids (ILs) as recyclable and highly efficient organocatalysts for the asymmetric Michael addition reactions. Tetrahedron Lett, 2008, 49: 1249-1252.
58. Kolb H C, Finn M G, Sharpless K B. Click chemistry: Diverse chemical function from a few good reactions. Angew Chem Int Ed, 2001, 40: 2004-2021.
59. Rostovtsev V V, Green L G, Fokin V V, et al. A stepwise Huisgen cycloaddition process: Copper (I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed, 2002, 41: 2596-2599.
60. Kolb H C, Sharpless K B. The growing impact of click chemistry on drug discovery. Drug Discovery Today, 2003, 8: 1128-1137.
61. Hawker C J, Wooley K L. The convergence of synthetic organic and polymer chemistries. Science, 2005, 309: 1200-1205.