Synthesis of β-Amino Alcohols from Value-Added Plant-Polyphenols Using ACC as a Green Reaction Medium and Mechanistic Study from DFT Analysis

References

• L. I. Kas’yan, V. A. Pal’chikov, and Y. S. Bondarenko, “Five-Membered Oxaza Heterocyclic Compounds on the Basis of Epoxides and Aziridines,” Russian Journal of Organic Chemistry 47, no. 6 (2011): 797–841. doi:10.1134/S1070428011060017.
   Web of Science ®Google Scholar
• D. Tanner, “Chiral Aziridines-Their Synthesis and Use in Stereoselective Transformations,” Angewandte Chemie International Edition in English 33, no. 6 (1994): 599–619. doi:10.1002/anie.199405991.
   Web of Science ®Google Scholar
• J. G. Smith, “Synthetically Useful Reactions of Epoxides,” Synthesis 8 (1984): 629–56.
   Google Scholar
• Girija S. Singh, Karen Mollet, Matthias D'hooghe, and Norbert De Kimpe, “Epihalohydrins in Organic Synthesis,” Chemical Reviews 113, no. 3 (2013): 1441–98. doi:10.1021/cr3003455.
   PubMed Web of Science ®Google Scholar
• Yun Chen, Wei-Qiang Zhang, Bin-Xun Yu, Yu-Ming Zhao, Zi-Wei Gao, Ya-Jun Jian, and Li-Wen Xu, “A Robust and Recyclable Polyurea-Encapsulated Copper(i) Chloride for One-Pot Ring-Opening/Huisgen Cycloaddition/CO2 Capture in Water,” Green Chemistry 18, no. 23 (2016): 6357–66. doi:10.1039/C6GC01956K.
   Google Scholar
• O. Mitsunobu, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, vol. 6, 88 (New York: Springer, 1991).
   Google Scholar
• D. J. Ager, I. Prakash, and D. R. Schaad, “1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis,” Chemical Reviews 96, no. 2 (1996): 835–75. doi:10.1021/cr9500038.
   PubMed Web of Science ®Google Scholar
• E. J. Corey, and F.-Y. Zhang, “Re- and si-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt: A Highly Stereoselective Synthesis of the HIV Protease Inhibitor Amprenavir (Vertex 478),” Angewandte Chemie International Edition 38, no. 13–14 (1999): 1931–4. doi:10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO;2-4.
   PubMed Web of Science ®Google Scholar
• P. O’Brine, “Sharpless Asymmetric Aminohydroxylation: Scope, Limitations, and Use in Synthesis,” Angewandte Chemie International Edition 38 (1999): 326–9.
   PubMed Web of Science ®Google Scholar
• J. F. J. Zhou, Y. Xiao, V. F. K. Yuen, G. Gökalp, X. Ma, S. Panda, T. T. Pham, N. Yan, and K. Zhou, “An Integrated Process for L-Tyrosine Production from Sugarcane Bagasse,” ACS Sustainable Chemistry & Engineering 9, no. 35 (2021): 11758–68. doi:10.1021/acssuschemeng.1c03098.
   Web of Science ®Google Scholar
• X. Chen, S. Song, H. Li, G. Gözaydın, and N. Yan, “Expanding the Boundary of Biorefinery: Organonitrogen Chemicals from Biomass,” Accounts of Chemical Research 54, no. 7 (2021): 1711–22. doi:10.1021/acs.accounts.0c00842.
   PubMed Web of Science ®Google Scholar
• Bee Lee Chng, and Arasu Ganesan, “Solution-Phase Synthesis of a β-Amino Alcohol Combinatorial Library,” Bioorganic and Medicinal Chemistry Letters 7, no. 12 (1997): 1511–4. doi:10.1016/S0960-894X(97)00260-6.
   Web of Science ®Google Scholar
• G. A. Rogers, S. M. Parsons, D. C. Anderson, L. M. Nilsson, B. A. Bahr, W. D. Kornreich, R. Kaufman, R. S. Jacobs, and B. Kirtman, “Synthesis, in Vitro Acetylcholine-Storage-Blocking Activities, and Biological Properties of Derivatives and Analogues of Trans-2-(4-Phenylpiperidino)cyclohexanol (Vesamicol)),” Journal of Medicinal Chemistry 32, no. 6 (1989): 1217–30. doi:10.1021/jm00126a013.
   PubMed Web of Science ®Google Scholar
• Jean De Crée, Hedwig Geukens, Jos Leempoels, and Herman Verhaegen, “Haemodynamic Effects in Man during Exercise of a Single Oral Dose of Narbivolol (R 67555), a New Beta-1-Adrenoceptor Blocking Agent: A Comparative Study with Atenolol, Pindolol, and Propranolol,” Drug Development Research 8, no. 1-4 (1986): 109–17. doi:10.1002/ddr.430080114.
   Web of Science ®Google Scholar
• X.-L. Fu, and S.-H. Wu, “A Regio-and Stereoselective Synthesis of β-Amino Alcohols,” Synthetic Communications 27, no. 10 (1997): 1677–83. doi:10.1080/00397919708004077.
   Web of Science ®Google Scholar
• P. Weghe, and J. Collin, “Ring Opening Reactions of Epoxides Catalyzed by Samarium Iodides,” Tetrahedron Letters 36, no. 10 (1995): 1649–52. doi:10.1016/0040-4039(95)00086-R.
   Web of Science ®Google Scholar
• L. Rajender Reddy, M. Arjun Reddy, N. Bhanumathi, and K. Rama Rao, “Cerium Chloride-Catalysed Cleavage of Epoxides with Aromatic Amines,” Synthesis 2001, no. 06 (2001): 0831–2. doi:10.1055/s-2001-13414.
   Google Scholar
• Massimo Curini, Francesco Epifano, Maria Carla Marcotullio, and Ornelio Rosati, “Zirconium Sulfophenyl Phosphonate as a Heterogeneous Catalyst in the Preparation of β-Amino Alcohols from Epoxides,” European Journal of Organic Chemistry 2001, no. 21 (2001): 4149–52. doi:10.1002/1099-0690(200111)2001:21<4149::AID-EJOC4149>3.0.CO;2-R.
   Web of Science ®Google Scholar
• M. Halder, P. Bhanja, S. Roy, S. Ghosh, S. Kundu, Md M. Islam, and Sk M. Islam, “A New Recyclable Functionalized Mesoporous SBA-15 Catalyst Grafted with Chiral Fe(Iii) Sites for the Enantioselective Aminolysis of Racemic Epoxides under Solvent Free Conditions,” RSC Advances 6, no. 100 (2016): 97599–605. doi:10.1039/C6RA23289B.
   Google Scholar
• G. Sekar, and Y. K. Singh, “An Efficient Method for Cleavage of Epoxides with Aromatic Amines,” The Journal of Organic Chemistry 64, no. 1 (1999): 287–9. doi:10.1021/jo981196c.
   PubMed Web of Science ®Google Scholar
• J. Augé, and F. Leroy, “Lithium Trifluoromethanesulfonate-Catalysed Aminolysis of Oxiranes,” Tetrahedron Letters 37, no. 43 (1996): 7715–6. doi:10.1016/0040-4039(96)01731-5.
   Web of Science ®Google Scholar
• Marco Chini, Paolo Crotti, Lucilla Favero, Franco Macchia, and Mauro Pineschi, “Lanthanide(III) Trifluoromethanesulfonates as Extraordinarily Effective New Catalysts for the Aminolysis of 1,2-Epoxides,” Tetrahedron Letters 35, no. 3 (1994): 433–6. doi:10.1016/0040-4039(94)85073-9.
   Web of Science ®Google Scholar
• T. Ollevier, and G. Lavie-Compin, “An Efficient Method for the Ring Opening of Epoxides with Aromatic Amines Catalyzed by Bismuth Trichloride,” Tetrahedron Letters 43, no. 44 (2002): 7891–3. doi:10.1016/S0040-4039(02)01896-8.
   Web of Science ®Google Scholar
• M. Chini, P. Crotti, and F. Macchia, “Regioalternating Selectivity in the Metal Salt Catalyzed Aminolysis of Styrene Oxide,” The Journal of Organic Chemistry 56, no. 20 (1991): 5939–42. doi:10.1021/jo00020a042.
   Web of Science ®Google Scholar
• S. Chandrasekhar, S. Ramachandar, and J. S. Prakash, “TaCl5-Catalyzed Cleavage of Epoxides with Aromatic Amines,” Synthesis 2000, no. 13 (2000): 1817–8. doi:10.1055/s-2000-8240.
   Google Scholar
• R. N. Swamy, G. Kondaji, and K. Nagaiah, “Bi3+ Catalyzed Regioselective Ring Opening of Epoxides with Aromatic Amines,” Synthetic Communications 32, no. 15 (2002): 2307–12. doi:10.1081/SCC-120006000.
   Web of Science ®Google Scholar
• H. Kotsuki, K. Hayashida, T. Shimanouchi, and H. Nishizawa, “High-Pressure Organic Chemistry. 19. High-Pressure-Promoted, Silica Gel-Catalyzed Reaction of Epoxides with Nitrogen Heterocycles,” The Journal of Organic Chemistry 61, no. 3 (1996): 984–90. doi:10.1021/jo951106t.
   Web of Science ®Google Scholar
• M. Shi, and Y. Chen, “Lewis Acids Catalyzed Ring-Opening Reactions of Methylenecyclopropanes and Epoxides in Supercritical Carbon Dioxide or Modified Supercritical Carbon Dioxide with Perfluorocarbon,” Journal of Fluorine Chemistry 122, no. 2 (2003): 219–27. doi:10.1016/S0022-1139(03)00083-6.
   Web of Science ®Google Scholar
• A. B. Reitz, M. A. Avery, R. P. Rosenkranz, M. S. Verlander, K. L. Melmon, B. B. Hoffman, Y. Akita, N. Castagnoli, and M. Goodman, “Conjugates of Catecholamines. 6. Synthesis and Beta-Adrenergic Activity of N-(Hydroxyalkyl)catecholamine Derivatives,” Journal of Medicinal Chemistry 28, no. 5 (1985): 642–7. doi:10.1021/jm50001a018.
   PubMed Web of Science ®Google Scholar
• Y.-H. Chen, C.-Y. Yang, C. W. Cheng, Y.-Y. Lin, S. L. Kuo, and L.-W. Hsin, “Identification of Buctopamine and Mebuctopamine, a β2 Receptor Agonist and Its Metabolite, in Swine Hair and Feed Additives,” Journal of Agricultural and Food Chemistry 65, no. 19 (2017): 3965–74. doi:10.1021/acs.jafc.7b00130.
   PubMed Web of Science ®Google Scholar
• K. Misra, H. S. Maity, S. Chanda, and A. Nag, “New Greener Alternatives for Bioreduction of Aromatic Aldehydes and Decarboxylation of Aromatic Acids Using Juice of Fruits,” Journal of Molecular Catalysis B: Enzymatic 82 (2012): 92–5. doi:10.1016/j.molcatb.2012.06.004.
   Google Scholar
• Roberta Bernini, Enrico Mincione, Maurizio Barontini, Gianfranco Provenzano, and Leonardo Setti, “Obtaining 4-Vinylphenols by Decarboxylation of Natural 4-Hydroxycinnamic Acids under Microwave Irradiation,” Tetrahedron 63, no. 39 (2007): 9663–7. doi:10.1016/j.tet.2007.07.035.
   Web of Science ®Google Scholar
• C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density,” Physical Review B 37, no. 2 (1988): 785–9. doi:10.1103/physrevb.37.785.
   PubMed Web of Science ®Google Scholar
• A. D. Becke, “Densityfunctional Thermochemistry. I. The Effect of the Exchangeonly Gradient Correction,” Journal of Chemical Physics 96, no. 3 (1992): 2155–60. doi:10.1063/1.462066.
   Web of Science ®Google Scholar
• F. Weigend, “Accurate Coulomb-Fitting Basis Sets for H to Rn,” Physical Chemistry Chemical Physics : PCCP 8, no. 9 (2006): 1057–65. doi:10.1039/b515623h.
   PubMed Web of Science ®Google Scholar
• F. Weigend, and R. Ahlrichs, “Balanced Basis Sets of Split Valence, Triple Zeta Valence and Quadruple Zeta Valence Quality for H to Rn: Design and Assessment of Accuracy,” Physical Chemistry Chemical Physics : PCCP 7, no. 18 (2005): 3297–305. doi:10.1039/b508541a.
   PubMed Web of Science ®Google Scholar
• M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, et al, 2010. Gaussian 09, Revision C.01 (Walling-ford, CT: Gaussian, Inc.).
   Google Scholar
• Bo Tang, Wei-Chao Song, Sheng-Yang Li, En-Cui Yang, and Xiao-Jun Zhao, “Post-Synthesis of Zr-MOR as a Robust Solid Acid Catalyst for the Ring-Opening Aminolysis of Epoxides,” New Journal of Chemistry 42, no. 16 (2018): 13503–11. doi:10.1039/C8NJ02449A.
   Web of Science ®Google Scholar
• G. Mancilla, M. Femenía-Ríos, A. J. Macías-Sánchez, and I. G. Collado, “Sn(OTf)2 Catalysed Regioselective Styrene Oxide Ring Opening with Aromatic Amines,” Tetrahedron 64, no. 51 (2008): 11732–7. doi:10.1016/j.tet.2008.09.099.
   Web of Science ®Google Scholar