Synthesis of α,β-diamino acid derivatives by acid-catalyzed Aza-Michael addition of N-phthalyldehydroalanine with different amine

Reference

• Harkiss, A. H.; Sutherland, A. Recent Advances in the Synthesis and Application of Fluorescent α-Amino Acids. Org. Biomol. Chem. 2016, 14, 8911–8921. DOI: 10.1039/c6ob01715k.
   PubMed Web of Science ®Google Scholar
• Verhoeven, J.; Hulpia, F.; Kersemans, K.; Bolcaen, J.; De Lombaerde, S.; Goeman, J.; Descamps, B.; Hallaert, G.; Van den Broecke, C.; Deblaere, K.; et al. New Fluoroethyl Phenylalanine Analogues as Potential LAT1-Targeting PET Tracers for Glioblastoma. Sci. Rep. 2019, 9, 2878. DOI: 10.1038/s41598-019-40013-x.
   PubMed Web of Science ®Google Scholar
• Brasile, G.; Mauri, L.; Sonnino, S.; Compostella, F.; Ronchetti, F. A Practi-Cal Route to Long-Chain Non-Natural α,ω-Diamino Acids. Amino Acids. 2013, 44, 435–441. DOI: 10.1007/s00726-012-1349-0.
   PubMed Web of Science ®Google Scholar
• Cheng, Z.; Kuru, E.; Sachdeva, A.; Vendrell, M. Fluorescent Amino Acids as Versatile Building Blocks for Chemical Biology. Nat. Rev. Chem. 2020, 4, 275–290. DOI: 10.1038/s41570-020-0186-z.
   PubMed Web of Science ®Google Scholar
• Jiang, J.; Ma, Z.; Castle, S. L. Bulky α, β-Dehydroamino Acids: Their Occurrence in Nature, Synthesis, and Applications. Tetrahedron 2015, 71, 5431–5451. DOI: 10.1016/j.tet.2015.06.001.
   Web of Science ®Google Scholar
• Viso, A.; Fernández de la Pradilla, R.; Tortosa, M.; García, A.; Flores, A. Update 1 of: α,β-Diamino Acids: biological Significance and Synthetic Approaches. Chem. Rev. 2011, 111, PR1–P42. DOI: 10.1021/cr100127y.
   PubMed Web of Science ®Google Scholar
• Zhou, F.; Hu, Q. L.; Hou, K. Q.; Chan, A. S. C.; Xiong, X. F. Construction of α,β-Diamino Diacid Derivatives with Adjacent Acyclic Tetrasubstituted Stereocenters. J. Org. Chem. 2022, 87, 8709–8718. DOI: 10.1021/acs.joc.2c00950.
   PubMed Web of Science ®Google Scholar
• Struble, T. J.; Smajlagic, I.; Foy, H.; Dudding, T.; Johnston, J. N. DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters. J. Org. Chem. 2021, 86, 15606–15617. DOI: 10.1021/acs.joc.1c02112.
   PubMed Web of Science ®Google Scholar
• Navo, C. D.; Oroz, P.; Mazo, N.; Blanco, M.; Peregrina, J. M.; Jiménez-Osés, G. Stereoselective α-Deuteration of Serine, Cysteine, Selenocysteine, and 2,3-Diaminopropanoic Acid Derivatives. Org. Lett. 2022, 24, 6810–6815. DOI: 10.1021/acs.orglett.2c02715.
   PubMedGoogle Scholar
• O’Brien, K.; Kelleher, F. Synthesis of Orthogonally Protected 1, 2-Diaminopropanoic Acids by Ring-Opening of 3-Unsubstituted N-Activated Aziridine 2-Carboxylates with Para-Methoxybenzylamine: A Study of the Regioselectivity of the Reaction. Tetrahedron Lett. 2013, 54, 6627–6630. DOI: 10.1016/j.tetlet.2013.09.116.
   Web of Science ®Google Scholar
• Wu, G.; Wang, J.; Liu, C.; Sun, M.; Zhang, L.; Ma, Y.; Cheng, R.; Ye, J. Transition Metal-Free, Visible-Light-Mediated Construction of α, β-Diamino Esters via Decarboxylative Radical Addition at Room Temperature. Org. Chem. Front. 2019, 6, 2245–2249. DOI: 10.1039/C9QO00407F.
   Web of Science ®Google Scholar
• Bonauer, C.; Walenzyk, T.; König, B. α,β-Dehydroamino Acids. Synthesis 2006, 2006, 1–20. DOI: 10.1055/s-2005-921759.
   Google Scholar
• Kotha, S.; Bandarugattu, V. B.; Krishna, N. G. Diversity-Oriented Approach to Unusual Amino Acid Derivatives and Heterocycles via Methyl 2-Acetamidoacrylate and Its Congeners. Tetrahedron 2014, 70, 5361–5384. DOI: 10.1016/j.tet.2014.05.056.
   Web of Science ®Google Scholar
• Lenartowicz, P.; Witkowska, D.; Żyszka-Haberecht, B.; Dziuk, B.; Ejsmont, K.; Świątek-Kozłowska, J.; Kafarski, P. A Novel Approach for Obtaining α,β-Diaminophosphonates Bearing Structurally Diverse Side Chains and Their Interactions with Transition Metal Ions Studied by ITC. RSC Adv. 2020, 10, 24045–24056. DOI: 10.1039/d0ra03764h.
   PubMed Web of Science ®Google Scholar
• Abreu, A. S.; Silva, N. O.; Ferreira, P. M.; Queiroz, M. J. R. Synthesis of Novel Amino Acids and Dehydroamino Acids Containing the Benzo [b] Thiophene Moiety. Eur. J. Org. Chem. 2003, 2003, 1537–1544. DOI: 10.1002/ejoc.200390212.
   Web of Science ®Google Scholar
• Ferreira, P. M.; Maia, H. L.; Monteiro, L. S.; Sacramento, J. Michael Addition of Thiols, Carbon Nucleophiles and Amines to Dehydroamino Acid and Dehydropeptide Derivatives. J. Chem. Soc., Perkin Trans. 1 2001, 23, 3167–3173. DOI: 10.1039/b106487h.
   Google Scholar
• Ferreira, P. M.; Maia, H. L.; Monteiro, L. S.; Sacramento, J.; Sebastião, J. Synthesis of β-Substituted Alanines via Michael Addition of Nucleophiles to Dehydroalanine Derivatives. J. Chem. Soc., Perkin Trans. 1 2000, 19, 3317–3324. DOI: 10.1039/b003353g.
   Google Scholar
• Asquith, R. S.; Yeung, K. W.; Otterburn, M. S. Synthesis, Identification and Properties of Some β-Aminoalanine Derivatives. Tetrahedron 1977, 33, 1633–1635. DOI: 10.1016/0040-4020(77)80175-0.
   Web of Science ®Google Scholar
• Asquith, R. S.; Carthew, P. Synthesis and PMR Properties of Some Dehyd-Roalanine Derivatives. Tetrahedron 1972, 28, 4769–4773. DOI: 10.1016/0040-4020(72)88085-2.
   Web of Science ®Google Scholar
• Pérez, M.; Pleixats, R. FeCl3-Catalyzed Conjugate Addition of Secondary Amines, Imidazole and Pyrazole to Methyl 2-Acetamidoacrylate. Preparation of β-Dialkylamino-Αalanine and β-(N-Heteroaryi)-α-Alanine Derivatives. Tetrahedron 1995, 51, 8355–8362. DOI: 10.1016/0040-4020(95)00446-F.
   Web of Science ®Google Scholar
• Ferreira, P. M.; Maia, H. L.; Monteiro, L. S. High Yielding Synthesis of Heterocyclic β-Substituted Alanine Derivatives. Tetrahedron Lett. 1999, 40, 4099–4102. DOI: 10.1016/S0040-4039(99)00691-7.
   Google Scholar
• Zhang, H.; Li, H.; Yang, H.; Fu, H. Iron-Catalyzed Diastereoselective Synthesis of Unnatural Chiral Amino Acid Derivatives. Org. Lett. 2016, 18, 3362–3365. DOI: 10.1021/acs.orglett.6b01493.
   PubMedGoogle Scholar
• Ferreira, P. M.; Maia, H. L.; Monteiro, L. S.; Sacramento, J. High Yielding Synthesis of Dehydroamino Acid and Dehydropeptide Derivatives. J. Chem. Soc., Perkin Trans. 1 1999, 24, 3697–3703. DOI: 10.1039/a904730a.
   Google Scholar
• Wabnitz, T. C.; Spencer, J. B. A General, Brønsted Acid-Catalyzed Hetero-Michael Addition of Nitrogen, Oxygen, and Sulfur Nucleophiles. Org. Lett. 2003, 5, 2141–2144. DOI: 10.1021/ol034596.
   PubMed Web of Science ®Google Scholar
• Choudhary, V. R.; Dumbre, D. K.; Patil, S. K. FeCl3/Montmorillonite K10as an Efficient Catalyst for Solvent-Free Aza-Michael Reaction between Amine and α,β-Unsaturated Compounds. RSC Adv. 2012, 2, 7061–7065. DOI: 10.1039/c2ra01323a.
   Web of Science ®Google Scholar
• Liu, X. B.; Lu, M.; Lu, T. T.; Gu, G. L. Functionalized Ionic Liquid Promoted Aza-Michael Addition of Aromatic Amines. J. Chin. Chem. Soc. 2010, 57, 1221–1226. DOI: 10.1002/jccs.201000180.
   Web of Science ®Google Scholar
• Azizi, N.; Baghi, R.; Ghafuri, H.; Bolourtchian, M.; Hashemi, M. Silicon Tetrachloride Catalyzed Aza-Michael Addition of Amines to Conjugated Alkenes under Solvent-Free Conditions. Synlett 2010, 2010, 379–382. DOI: 10.1055/s-0029-1219195.
   Google Scholar
• Wabnitz, T. C.; Yu, J. Q.; Spencer, J. B. Evidence That Protons Can Be the Active Catalysts in Lewis Acid Mediated Hetero-Michael Addition Reactions. Chemistry 2004, 10, 484–493. DOI: 10.1002/chem.200305407.
   PubMed Web of Science ®Google Scholar