Histidine-based salt as an ionic tag for proline: application in enantioselective cross aldol reaction in ionic liquids

References

• Yamashita, Y.; Yasukawa, T.; Yoo, W.-J.; Kitanosono, T.; Kobayashi, S. Catalytic Enantioselective Aldol Reactions. Chem. Soc. Rev. 2018, 47, 4388–4480. DOI: 10.1039/C7CS00824D.
   PubMed Web of Science ®Google Scholar
• Clapès, P.; Joglar, J. Enzyme-Catalyzed Aldol Additions. In Modern Methods in Stereoselective Aldol Reactions, Mahrwald, R., Ed.; Wiley-VCH: Berlin, 2013; ch. 8, pp. 475–527.
   Google Scholar
• Tanaka, A.; Barbas, C. F. III. Antibody-Catalyzed Aldol Reactions. In Modern Aldol Reactions, Mahrwald, R., Ed.; Wiley-VCH: Berlin, 2004; Vol. 1, ch. 6, pp. 273–310.
   Google Scholar
• Trost, B. M.; Brindle, C. S. The Direct Catalytic Asymmetric Aldol Reaction. Chem. Soc. Rev. 2010, 39, 1600–1632. DOI: 10.1039/b923537j.
   PubMed Web of Science ®Google Scholar
• (a) Guillena, G.; Najera, C.; Ramon, D. J. Enantioselective Direct Aldol Reaction: The Blossoming of Modern Organocatalysis. Tetrahedron: Asym. 2007, 18, 2249–2293. DOI: 10.1016/j.tetasy.2007.09.025.
   Web of Science ®Google Scholar
  (b) Guillena, G. Organocatalyzed Aldol Reactions. In Modern Methods in Stereoselective Aldol Reactions, Mahrwald, R., Ed.; Wiley-VCH: Berlin, 2013; ch. 3, pp. 155–268.
   Google Scholar
• (a) Luppi, G.; Cozzi, P. G.; Monari, M.; Kaptein, B.; Broxterman, Q. B.; Tomasini, C. J. Dipeptide-Catalyzed Asymmetric Aldol Condensation of Acetone with (N-Alkylated) Isatins. J. Org. Chem. 2005, 70, 7418–7421. DOI: 10.1021/jo050257l.
   PubMed Web of Science ®Google Scholar
  (b) Zou, W.; Ibrahem, I.; Dziedzic, P.; Sunden, H.; Cordova, A. Small Peptides as Modular Catalysts for the Direct Asymmetric Aldol Reaction: Ancient Peptides with Aldolase Enzyme Activity. Chem. Commun. 2005, 4946–4948. DOI: 10.1039/b509920j.
   PubMed Web of Science ®Google Scholar
  (c) Cordova, A.; Zou, W.; Dziedzic, P.; Ibrahem, I.; Reyes, E.; Xu, Y. Direct Asymmetric Intermolecular Aldol Reactions Catalyzed by Amino Acids and Small Peptides. Chem. Eur. J. 2006, 12, 5383–5397. DOI: 10.1002/chem.200501639.
   PubMed Web of Science ®Google Scholar
  (d) Dziedzic, P.; Zou, W.; Hafren, J.; Cordova, A. The Small Peptide-Catalyzed Direct Asymmetric Aldol Reaction in Water. Org. Biomol. Chem. 2006, 4, 38–40. DOI: 10.1039/B515880J.
   PubMed Web of Science ®Google Scholar
  (e) Wu, F.-C.; Da, C.-S.; Du, Z.-X.; Guo, Q.-P.; Li, W.-P.; Yi, L.; Jia, Y.-N.; Ma, X. N -Primary-Amine-Terminal β-Turn Tetrapeptides as Organocatalysts for Highly Enantioselective Aldol Reaction. J. Org. Chem. 2009, 74, 4812–4818. DOI: 10.1021/jo9005766.
   PubMed Web of Science ®Google Scholar
  (f) Bisticha, A.; Triandafillidi, I.; Kokotos, C. G. tert-Butyl Esters of Peptides as Organocatalysts for the Asymmetric Aldol Reaction. Tetrahedron: Asym 2015, 26, 102–108. DOI: 10.1016/j.tetasy.2014.12.007.
   Web of Science ®Google Scholar
  (g) Kon, K.; Kohari, Y.; Murata, M. Unnatural Tripeptide as Highly Enantioselective Organocatalyst for Asymmetric Aldol Reaction of Isatins. Tetrahedron Lett. 2019, 60, 415–418. DOI: 10.1016/j.tetlet.2018.12.049.
   Web of Science ®Google Scholar
• (a) Benaglia, M.; Puglisi, A.; Cozzi, F. Polymer-Supported Organic Catalysts †. Chem. Rev. 2003, 103, 3401–3430. DOI: 10.1021/cr010440o.
   PubMed Web of Science ®Google Scholar
  (b) Gruttadauria, M.; Giacalone, F.; Noto, R. Supported Proline and Proline-Derivatives as Recyclable Organocatalysts. Chem. Soc. Rev. 2008, 37, 1666–1688. DOI: 10.1039/b800704g.
   PubMed Web of Science ®Google Scholar
  (c) Ferré, M.; Pleixats, R.; Wong Chi Man, M.; Cattoën, X. Recyclable Organocatalysts Based on Hybrid Silicas. Green Chem. 2016, 18, 881–922. DOI: 10.1039/C5GC02579F.
   Web of Science ®Google Scholar
• Bergbreiter, D. E.; Tian, J.; Hongfa, C. Using Soluble Polymer Supports to Facilitate Homogeneous Catalysis. Chem. Rev. 2009, 109, 530–582. DOI: 10.1021/cr8004235.
   PubMed Web of Science ®Google Scholar
• (a) Chu, Q.; Zhang, W.; Curran, D. P. A Recyclable Fluorous Organocatalyst for Diels–Alder Reactions. Tetrahedron Lett 2006, 47, 9287–9290. DOI: 10.1016/j.tetlet.2006.10.101.
   PubMed Web of Science ®Google Scholar
  (b) Miranda, P. O.; Llanes, P.; Torkian, L.; Pericàs, M. A. A Fluorous Proline Organocatalyst with Acetone-Dependent Aldolase Behavior. Eur. J. Org. Chem. 2013, 2013, 6254–6258. DOI: 10.1002/ejoc.201301041.
   Web of Science ®Google Scholar
  (c) Huang, X.; Liu, M.; Jasinski, J. P.; Peng, B.; Zhang, W. Recyclable Organocatalysts for a One-Pot Asymmetric Synthesis of 2-Fluorocyclohexanols Bearing Six Contiguous Stereocenters. Adv. Synth. Catal. 2017, 359, 1919–1926. DOI: 10.1002/adsc.201700129.
   Web of Science ®Google Scholar
• (a) Huo, C.; Chan, T. H. A Novel Liquid-Phase Strategy for Organic Synthesis Using Organic Ions as Soluble Supports. Chem. Soc. Rev. 2010, 39, 2977–3006. DOI: 10.1039/b914497h.
   PubMed Web of Science ®Google Scholar
  (b) Karimi, B.; Tavakolian, M.; Akbari, M.; Mansouri, F. Ionic Liquids in Asymmetric Synthesis: An Overall View from Reaction Media to Supported Ionic Liquid Catalysis. ChemCatChem 2018, 10, 3173–3205. DOI: 10.1002/cctc.201701919.
   Web of Science ®Google Scholar
• (a) Miao, W.; Chan, T. H. Ionic-Liquid-Supported Organocatalyst: Efficient and Recyclable Ionic-Liquid-Anchored Proline for Asymmetric Aldol Reaction. Adv. Synth. Catal. 2006, 348, 1711–1718. DOI: 10.1002/adsc.200606059.
   Web of Science ®Google Scholar
  (b) Eyckens, D. J.; Brozinski, H. L.; Delaney, J. P.; Servinis, L.; Naghashian, S.; Henderson, L. C. Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water. Catal. Lett. 2016, 146, 212–219. DOI: 10.1007/s10562-015-1630-4.
   Web of Science ®Google Scholar
• (a) Luo, S.; Mi, X.; Zhang, L.; Liu, S.; Xu, H.; Cheng, J.-P. Functionalized Chiral Ionic Liquids as Highly Efficient Asymmetric Organocatalysts for Michael Addition to Nitroolefins. Angew. Chem. Int. Ed. 2006, 45, 3093–3097. DOI: 10.1002/anie.200600048.
   PubMed Web of Science ®Google Scholar
  (b) Luo, S.; Mi, X.; Zhang, L.; Liu, S.; Xu, H.; Cheng, J.-P. Functionalized Ionic Liquids Catalyzed Direct Aldol Reactions. Tetrahedron 2007, 63, 1923–1930. DOI: 10.1016/j.tet.2006.12.079.
   Web of Science ®Google Scholar
  (c) Ni, B.; Zhang, Q.; Headley, A. D. Functionalized Chiral Ionic Liquid as Recyclable Organocatalyst for Asymmetric Michael Addition to Nitrostyrenes. Green Chem. 2007, 9, 737–739. DOI: 10.1039/b702081c.
   Web of Science ®Google Scholar
• (a) 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. DOI: 10.1002/adsc.200700136.
   Web of Science ®Google Scholar
  (b) Zhou, L.; Wang, L. Chiral Ionic Liquid Containing L-Proline Unit as a Highly Efficient and Recyclable Asymmetric Organocatalyst for Aldol Reaction. Chem. Lett. 2007, 36, 628–629. DOI: 10.1246/cl.2007.628.
   Web of Science ®Google Scholar
  (c) Kucherenko, A. S.; Perepelkin, V. V.; Zhdankina, G. M.; Kryshtal, G. V.; Srinivasan, E.; Inani, H.; Zlotin, S. G. Ionic Liquid Supported 4-HO-Pro-Val Derived Organocatalysts for Asymmetric Aldol Reactions in the Presence of Water. Mendeleev Commun. 2016, 26, 388–390. DOI: 10.1016/j.mencom.2016.09.007.
   Web of Science ®Google Scholar
  (d) Yadav, G. D.; Singh, S. (L)-Prolinamide Imidazolium Hexafluorophosphate Ionic Liquid as an Efficient Reusable Organocatalyst for Direct Asymmetric Aldol Reaction in Solvent-Free Condition. RSC Adv. 2016, 6, 100459–100466. DOI: 10.1039/C6RA23652A.
   Web of Science ®Google Scholar
  (e) Obregón-Zúñiga, A.; Juaristi, E. (2S,4R)-Hyp-(S)-Phe-OMe Dipeptide Supported on Imidazolium Tagged Molecules as Recoverable Organocatalysts for Asymmetric Aldol Reactions Using Water as Reaction Medium. Tetrahedron 2017, 73, 5373–5380. DOI: 10.1016/j.tet.2017.07.037.
   Web of Science ®Google Scholar
• (a) Guillen, F.; Brégeon, D.; Plaquevent, J.-C. (S)-Histidine: The Ideal Precursor for a Novel Family of Chiral Aminoacid and Peptidic Ionic Liquids. Tetrahedron Lett. 2006, 47, 1245–1248. DOI: 10.1016/j.tetlet.2005.12.090.
   Web of Science ®Google Scholar
  (b) Brégeon, D.; Levillain, J.; Guillen, F.; Plaquevent, J.-C.; Gaumont, A.-C. Thiazolinium and Imidazolium Chiral Ionic Liquids Derived from Natural Amino Acid Derivatives. Amino Acids 2008, 35, 175–184. DOI: 10.1007/s00726-007-0575-3.
   PubMed Web of Science ®Google Scholar
  (c) Zgonnik, V.; Gonella, S.; Mazières, M.-R.; Guillen, F.; Coquerel, G.; Saffon, N.; Plaquevent, J.-C. Design and Scalable Synthesis of New Chiral Selectors. Part 2: Chiral Ionic Liquids Derived from Diaminocyclohexane and Histidine. Org. Process Res. Dev. 2012, 16, 277–285. DOI: 10.1021/op200082a.
   Web of Science ®Google Scholar
• List, B.; Lerner, R. A.; Barbas, C. F. III. Proline-Catalyzed Direct Asymmetric Aldol Reactions. J. Am. Chem. Soc. 2000, 122, 2395–2396. DOI: 10.1021/ja994280y.
   Web of Science ®Google Scholar
• (a) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Asymmetric Catalysis Special Feature Part II: Enantioselective Direct Aldol Reactions Catalyzed by L-Prolinamide Derivatives. Proc. Natl. Acad. Sci. USA 2004, 101, 5755–5760. DOI: 10.1073/pnas.0307176101.
   PubMed Web of Science ®Google Scholar
  (b) Mossé, S.; Alexakis, A. Organocatalyzed Asymmetric Reactions via Microwave Activation. Org. Lett. 2006, 8, 3577–3580. DOI: 10.1021/ol0614727.
   PubMed Web of Science ®Google Scholar
  (c) 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, 210–215. DOI: 10.1002/asia.200600077.
   PubMed Web of Science ®Google Scholar