(S)-5-prolylamide-triazole organocatalyst for direct asymmetric aldol reactions

Current Organic Chemistry

Volumn 17, Issue 14, 2013, Pages 1563-1568

  Liu, Ling ^a   Gao, Min Na ^a   Li, Yang ^a   Li, Zhen ^a   Song, Liping ^a   Liu, Zhong Wen ^a,b   Xue, Dong ^a,b   Liu, Zhao Tie ^a,b  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^b SHAANXI NORMAL UNIVERSITY   (China)

Author keywords

(S) 5 prolylamide triazole; Asymmetric aldol reaction; Enantiomeric excess (ee) value; Organocatalyst; Proline derivative

Indexed keywords

ACETONE; CONDENSATION REACTIONS; ENANTIOMERS; SOLVENTS;

(S)-5-PROLYLAMIDE-TRIAZOLE; AROMATIC ALDEHYDE; ASYMMETRIC ALDOL REACTIONS; CATALYST LOADINGS; ENANTIOMERIC EXCESS; ENANTIOMERIC EXCESS VALUE; ORGANOCATALYSTS; PROLINE DERIVATIVES; SYNTHESISED; ]+ CATALYST;

ORGANOCATALYST;

EID: 84881329074     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272811317140011     Document Type: Article

References (64)

1. Dalko, P. I.; Moisan, L. Enantioselective Organocatalysts. Angew. Chem., Int. Ed., 2001, 40, 3726-3748.
2. List, B. Enamine Catalysis is a Powerful Strategy for the Catalytic Generation and Use of Carbanion Equivalents. Acc. Chem. Res., 2004, 37, 548-557
3. Saito, S.; Yamamoto, H. Design of Acid-base Catalysis for the Asymmetric Direct AldolReaction. Acc. Chem. Res., 2004, 37, 570-579
4. Notz, W.; Tanaka, F.; Barbas, C. F. III. Enamine-Based Organocatalysis with Proline and Diamines:The Development of Direct Catalytic Asymmetric Aldol, Mannich, Michael and Diels-Alder Reactions. Acc. Chem. Res., 2004, 37, 580-591.
5. List, B.; Lerner, R. A.; Barbas, C. F., III. Proline-Catalyzed Direct Asymmetric Aldol Reactions. J. Am. Chem. Soc., 2000, 122, 2395-2396
6. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. Amino Acid Catalyzed Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions. J. Am. Chem. Soc., 2001, 123, 5260-5267
7. Northrup, A. B.; Casas, J.; Sunden, H.; Córdova, A. Direct Organocatalytic Asymmetric alpha-Hydroxymethylation of Ketones and Aldehydes. Tetrahedron Lett., 2004, 45, 6117-6119.
8. Hartikka, A.; Arvidsson, P. I. 5-(Pyrrolidine-2-yl)tetrazole: Rationale for the Increased Reactivity of the Tetrazole Analogue of Proline in Organocatalyzed Aldol Reactions. Eur. J. Org. Chem., 2005, 20, 4287-4295.
9. Lacoste, E.; Landais, Y.; Schenk, K.; Verlhac, J. B.; Vincent, J. M. Benzoimidazole-Pyrrolidine (BIP), a High Reactive Chiral Organocatalyst. Tetrahedron Lett., 2004, 45, 8035-8038.
10. Chen, J. R.; Lu, H. H.; Li, X. Y.; Cheng, L.; Wan, J.; Xiao, W. J. Readily Tunable and Bifunctional L-Prolinamide Derivatives: Design and Application in the Direct Enantioselective Aldol Reactions. Org. Lett., 2005, 7, 4543-4545
11. Singh Chimni, S.; Mahajan, D.; Suresh Babu, V. V. Protonated Chiral Prolinamide Catalyzed Enantioselective Direct Aldol Reaction in Water. Tetrahedron Lett., 2005, 46, 5617-5619
12. 2-Symmetric Bisprolinamide as a Highly Efficient Catalyst for Direct Aldol Reaction. Org. Lett., 2005, 7, 5321-5323.
13. Jiang, J.; He, L.; Luo, S. W.; Cun, L. F.; Gong, L. Z. Enantioselective Desymmetrization of Prochiral Cyclohexanone Derivatives Via the Organocatalytic Direct Aldol Reaction. Chem. Commun., 2007, 736-738
14. Dodda, R.; Zhao, C. G. Organocatalytic Highly Enantioselective Synthesis of Secondary α-Hydroxyphosphonates. Org. Lett., 2006, 8, 4911-4914
15. Guizzetti, S.; Benaglia, M.; Raimondi, L.; Celentano, G. Enantioselective Direct Aldol Reaction "on water" Promoted by Chiral Organic Catalyst. Org. Lett., 2007, 9, 1247-1250
16. Maya, V.; Raj, M.; Singh, V. K. Highly Enantioselective Organocatalytic Direct Aldol Reaction in an Aqueous Medium. Org. Lett., 2007, 9, 2593-2595
17. Russo, A.; Botta, G.; Lattanzi, A. NOBIN-Prolinamide Organocatalyzed Enantioselective Direct Aldol Reaction: Remarkable Activity in Apolar Medium. Synlett., 2007, 5, 795-799.
18. Bisai, V.; Bisai, A.; Singh, V. K. Enantioselective Organocatalytic Aldol Reaction Using Small Organic Molecules. Tetrahedron, 2012, 68(24), 4541-4580.
19. Bhanushali, M.; Zhao, C. G. Developing Novel Organocatalyzed Aldol Reactions for the Enantioselective Synthesis of Biologically Active Molecules. Synth., 2011, (12), 1815-1830.
20. Gryko, D.; Chromíski, M.; Pielacíska, D. J. Prolinethioamides versus Prolinamides in Organocatalyzed Aldol Reactions-A Comparative Study. Symmetry, 2011, 3(2), 265-282.
21. Silva, F.; Sawicki, M.; Gouverneur, V. Enantioselective Organocatalytic Aldol Reaction of Ynones and its Synthetic Applications. Org. Lett., 2006, 8, 5417-5419
22. Wang, X. J.; Zhao, Y.; Liu, J. T. Regiospecific Organocatalytic Asymmetric Aldol Reaction of Methyl Ketones and α, β-Unsaturated Trifluoromethyl Ketones. Org. Lett., 2007, 9, 1343-1345.
23. Hayashi, Y.; Sumiya, T.; Takahashi, J.; Gotoh, H.; Urushima, T.; Shoji, M. Highly Diastereo-and Enantioselective Direct Aldol Reactions in Water. Angew. Chem. Int. Ed., 2006, 45, 958-961
24. Font, D.; Jimeno, C.; Pericàs, M. A. Polystyrene-supported Hydroxyproline: An Insoluble, Recyclable Organocatalyst for the Asymmetric Aldol Reaction in Water. Org. Lett., 2006, 8, 4653-4655
25. Gu, L. Q.; Yu, M. L.; Wu, X. Y.; Zhang, Y. Z.; Zhao, G. 4,4'-Disubstituted L-Prolines as Highly Enantioselective Catalysts for Direct Aldol Reactions. Adv. Synth. Catal., 2006, 348, 2223-2228
26. Lombardo, M.; Pasi, F.; Easwar, S.; Trombini, C. An Improved Protocol for the Direct Asymmetric Aldol Reaction in Ionic Liquids, Catalysed by Onium Ion-Tagged Prolines. Adv. Synth. Catal., 2007, 349, 2061-2065
27. Yoshitomi, Y.; Makino, K.; Hamada, Y. Organocatalytic Synthesis of (2S, 3R)-3-Hydroxy-3-methyl-proline (OHMePro), a Component of Polyoxypeptins, and Relatives Using OHMePro Itself as a Catalyst. Org. Lett., 2007, 9, 2457-2460.
28. Krattiger, P.; Kovasy, R.; Revell, J. D.; Ivan, S.; Wennemers, H. Increased Structural Complexity Leads to Higher Activity: Peptides as Efficient and Versatile Catalysts for Asymmetric Aldol Reactions. Org. Lett., 2005, 7, 1101-1103
29. Córdova, A.; Zou, W. B.; Dziedzic, P.; Ibrahem, I.; Reyes, E.; Xu, Y. M. Direct Asymmetric Intermolecular Aldol Reactions Catalyzed by Amino Acids and Small Peptides. Chem. Eur. J., 2006, 12, 5383-5397
30. 2 as A Catalyst for Aldol Reactions. Tetrahedron, 2007, 63, 8420-8424
31. Lei, M.; Shi, L. X.; Li, G.; Chen, S. L.; Fang, W. H.; Ge, Z. M.; Cheng, T. M.; Li, R. T. Dipeptidecatalyzed Direct Asymmetric Aldol Reactions in the Presence of Water. Tetrahedron, 2007, 63, 7892-7898
32. Andreae, M. R. M.; Davis, A. P. Heterogeneous Catalysis of the Asymmetric Aldol Reaction by Solidsupported Proline-terminated Peptides. Tetrahedron: Asymmetry., 2005, 16, 2487-2492.
33. Kano, T.; Yamaguchi, Y.; Tanaka, Y.; Maruoka, K. syn-Selective and Enantioselective Direct Cross-Aldol Reactions between Aldehydes Catalyzed by an Axially Chiral Amino Sulfonamide. Angew. Chem. Int. Ed. 2007, 46, 1738-1740
34. Ramasastry, S. S. V.; Albertshofer, K.; Utsumi, N.; Tanaka, F.; Barbas, C. F. III. Angew. Mimicking Fructose and Rhamnulose Aldolases: Organocatalytic syn-Aldol Reactions with Unprotected Dihydroxyacetone. Angew. Chem. Int. Ed., 2007, 46, 5572-5575
35. Kano, T.; Tokuda, O.; Takai, J.; Maruoka, K. Design of a Binaphthyl-Based Axially Chiral Amino Acid as an Organocatalyst for Direct Asymmetric Aldol Reactions. Chem. Asian. J., 2006, 1-2, 210-215
36. Jiang, Z. Q.; Liang, Z. A.; Wu, X. Y.; Lu, Y. X. Asymmetric Aldol Reactions Catalyzed by Tryptophan in Water. Chem. Commun., 2006, 2801-2803
37. +), a Highly Reactive Organocatalyst for Asymmetric Processes. Eur. J. Org. Chem., 2007, 1, 167-177
38. Nagamine, T.; Inomata, K.; Endo, Y.; Paquette, L. A. Amino Acid Mediated Intramolecular Asymmetric Aldol Reaction to Construct a New Chiral Bicyclic Enedione Containing a Seven-Membered Ring: Remarkable Inversion of Enantioselectivity Compared to the Six-Membered Ring Example. J. Org. Chem., 2007, 72, 123-131
39. Gryko, D.; Zimnicka, M.; Lipiβski, R. Brønsted Acids as Additives for the Direct Asymmetric Aldol Reaction Catalyzed by LProlinethioamides. Direct Evidence for Enamine-Iminium Catalysis. J. Org. Chem., 2007, 72, 964-970.
40. Hernandez, J. G.; Juaristi, E. Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-Containing Dipeptides: Improved Stereoinduction under Solvent-Free Conditions. J. Org. Chem., 2011, 76, 1464-1467.
41. Hernandez, J. G.; García-Lopez, V.; Juaristi, E. Solvent-free Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-containing Thiodipeptides under Ball-milling Conditions. Tetrahedron, 2012, 68, 92-97.
42. Hernandez, J. G.; Juaristi, E. Efficient Ball-mill Procedure in the 'Green' Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-containing Dipeptides in the Presence of Water. Tetrahedron, 2011, 67, 6953-6959.
43. Luo, S. Z.; Xu, H.; Li, J. Y.; Zhang, L.; Cheng, J. P. A Simple Primary Tertiary Diamine Brønsted Acid Catalyst for Asymmetric Direct Aldol Reactions of Linear Aliphatic Ketones. J. Am. Chem. Soc., 2007, 129, 3074-3075.
44. Ooi, T.; Taniguchi, M.; Kameda, M.; Maruoka, K. Direct Asymmetric Aldol Reactions of Glycine Schiff Base with Aldehydes Catalyzed by Chiral Quaternary Ammonium Salts. Angew. Chem. Int. Ed., 2002, 41, 4542-4544.
45. Tang, Z.; Jiang, F.; Yu, L. T.; Cui, X.; Gong, L. Z.; Mi, A. Q.; Jiang, Y. Z.; Wu, Y. D. Direct Asymmetric Aldol Reactions of Glycine Schiff Base with Aldehydes Catalyzed by Chiral Quaternary Ammonium Salts. J. Am. Chem. Soc., 2003, 125, 5262-5263
46. Tang, Z.; Yang, Z. H.; Chen, X. H.; Cun, L. F.; Mi, A. Q.; Jiang, Y. Z.; Gong, L. Z. A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones with Aldedydes. J. Am. Chem. Soc., 2005, 127 (25), 9285-9289
47. Jiang, M.; Zhu, S. F.; Yang, Y.; Gong, L. Z.; Zhou, X. G.; Zhou, Q. L., Asymmetric Aldol Reactions Catalyzed by New Spiro Diamine Derivatives. Tetrahedron: Asymmetry, 2006, 17, 384-387.
48. 2-Symmetrical Bisprolinamide Organocatalyst. Adv. Synth. Catal., 2012, 354, 197-204.
49. Delaney, J. P.; Henderson, L. C. Investigating Ionic Effects Applied to Water Based Organocatalysed Aldol Reactions. Int. J. Mol. Sci., 2011, 12, 9083-9094.
50. Lei, M.; Shi, L. X.; Li, G.; Chen, S. L.; Fang, W. H.; Ge, Z. M.; Cheng, T. M.; Li, R. T. Dipeptide-catalyzed Direct Asymmetric Aldol Reactions in the Presence of Water. Tetrahedron, 2007, 63, 7892-7898.
51. Wu, Y. Y.; Zhang, Y. H.; Yu, M. L.; Zhao, G.; Wang, S. W. Highly Efficient and Reusable Dendritic Catalysts Derived from N-Prolylsulfonamide for the Asymmetric Direct Aldol Reaction in Water. Org. Lett., 2006, 8, 4417-4420.
52. Pihko, P. M. Activation of Carbonyl Compounds by Double Hydrogen Bonding: An Emerging Tool in Asymmetric Catalysis. Angew. Chem., Int. Ed., 2004, 43, 2062-2064.
53. Akiyama, T.; Saitoh, Y.; Morita, H.; Fuchibe, K. Enantioselective Mannich-Type Reaction Catalyzed by a Chiral Brønsted Acid Derived from TADDOL. Adv. Synth. Catal., 2005, 347, 1523-1526.
54. Akiyama, T.; Tamura, Y.; Itoh, J.; Morita, H.; Fuchibe, K. Enantioselective Aza-Diels-Alder ReactionCatalyzed by a Chiral Brønsted Acid: Effect of the Additive on the Enantioselectivity. Synlett., 2006, 141-143.
55. Rueping, M.; Sugiono, E.; Azap, C.; Heissmann, T.; Bolte, M. Enantioselective Brønsted Acid Catalyzed Transfer Hydrogenation: Organocatalytic Reduction of Imines. Org. Lett., 2005, 7, 3781-3783.
56. McDougal, N. T.; Schaus, S. E. Asymmetric Morita Baylis Hillman Reactions Catalyzed by Chiral Brønsted Acids. J. Am. Chem. Soc., 2003, 125, 12094-12095
57. McDougal, N. T.; Trevellini, W. L.; Rodgen, S. A.; Kliman, L. T.; Schaus, S. E. The Development of the Asymmetric Morita-Baylis-Hillman Reaction Catalyzed by Chiral Brønsted Acids. Adv. Synth. Catal. 2004, 346, 1231-1240
58. Matsui, K.; Tanaka, K.; Horii, A.; Takizawa, S.; Sasai, H. Conformational Lock in a Brønsted Acid-Lewis Base Organocatalyst for the Aza-Morita-Baylis-Hillman Reaction. Tetrahedron: Asymmetry, 2006, 17, 578-583
59. Matsui, K.; Akizawa, S.; Sasai, H. A Brønsted Acid and Lewis Base Organocatalyst for the Aza-Morita-Baylis-Hillman Reaction. Synlett., 2006, 761-765.
60. Hine, J.; Linden, S. M.; Kanagasabapathy, V. M. Double-hydrogenbonding Catalysis of the Reaction of Phenyl Glycidyl Ether with Diethylamine by 1,8-Biphenylenediol. J. Org. Chem., 1985, 50, 5096-5099
61. Hine, J.; Ahn, K. The Double Hydrogen Bonding Ability of 4,5-Dinitro-1,8-biphenylenediol. J. Org. Chem., 1987, 52, 2083-2086
62. Suzuki, T.; Yamagiwa, N.; Matsuo, Y.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M.; Noyori, R. Catalytic Asymmetric Aldol Reaction of Ketones and Aldehydes Using Chiral Calcium Alkoxides. Tetrahedron Lett., 2001, 42, 4669-4671
63. Braddock, D. C.; MacGilp, I. D.; Perry, B. G. Planar Chiral PHANOLs as Organocatalysts for the Diels-Alder Reaction via Double Hydrogen-Bonding to a Carbonyl Group. Synlett., 2003, 1121-1124.
64. Zhou, Y.; Shan, Z. (R)-or (S)-Bi-2-naphthol Assisted, L-Proline Catalyzed Direct Aldol Reaction. Tetrahedron: Asymmetry, 2006, 17, 1671-1677.