Asymmetric Diels–Alder reaction of chalcone and isoprene mediated by titanium-based complexes

References

• Chee, C. F.; Abdullah, I.; Buckle, M. J. C.; Abd Rahman, N. An Efficient Synthesis of (+/-)-Panduratin A and (+/-)-Isopanduratin A, Inhibitors of Dengue-2 Viral Activity. Tetrahedron Lett. 2010, 51, 495–498. DOI: 10.1016/j.tetlet.2009.11.030.
   Web of Science ®Google Scholar
• Cong, H.; Becker, C. F.; Elliott, S. J.; Grinstaff, M. W.; Porco, J. A. Silver Nanoparticle-Catalyzed Diels-Alder Cycloadditions of 2'-Hydroxychalcones. J. Am. Chem. Soc. 2010, 132, 7514–7518. DOI: 10.1021/ja102482b.
   PubMed Web of Science ®Google Scholar
• Thy, C. K.; Murthy, S.; Lee, Y. K.; Yaeghoobi, M.; Abd Rahman, N.; Chee, C. F. A Simple Aluminum Bromide-Promoted Diastereoselective Synthesis of Panduratin A Derivatives. Synlett 2018, 29, 1358–1361. DOI: 10.1055/s-0036-1591561.
   Web of Science ®Google Scholar
• Jung, E. M.; Lee, Y. R. First Concise Total Syntheses of Biologically Interesting Nicolaioidesin C, Crinatusin C-1, and Crinatusin C-2. Bull. Korean Chem. Soc. 2008, 29, 1199–1204.
   Web of Science ®Google Scholar
• Pigott, A. J.; Lepage, R. J.; White, J. M.; Coster, M. J. Total Synthesis of (+/−)-Nicolaioidesin B via a Highly Regio- and Diastereoselective Diels-Alder Reaction. Tetrahedron Lett. 2014, 55, 6864–6867. DOI: 10.1016/j.tetlet.2014.10.097.
   Google Scholar
• Cong, H.; Ledbetter, D.; Rowe, G. T.; Caradonna, J. P.; Porco, J. A. Electron Transfer-Initiated Diels-Alder Cycloadditions of 2 '-Hydroxychalcones. J. Am. Chem. Soc. 2008, 130, 9214–9215. +. DOI: 10.1021/ja803094u.
   PubMed Web of Science ®Google Scholar
• Bavikar, S. R.; Lo, H.-J.; Sai Pavan Kumar, C. N. S.; Chein, R.-J. Total Synthesis of (-)-Panduratin D. Chem. Commun. (Camb) 2022, 58, 8564–8567. DOI: 10.1039/d2cc02980d.
   PubMed Web of Science ®Google Scholar
• Chai, G.-L.; Qiao, Y.; Zhang, P.; Guo, R.; Wang, J.; Chang, J. Chiral Hydroxytetraphenylene-Boron Complex Catalyzed Asymmetric Diels-Alder Cycloaddition of 2'-Hydroxychalcones. Org. Lett. 2020, 22, 8023–8027. DOI: 10.1021/acs.orglett.0c02978.
   PubMed Web of Science ®Google Scholar
• Li, X.; Liu, W.-X.; Wang, C.-C.; Wei, J.-X.; Wu, Y.-Q.; Xiao, Z.-Y.; Li, K.; Li, Y.-X.; Li, L.-Z. Catalytic Asymmetric Diels-Alder Reaction of 2'-Hydroxychalcone as a Dienophile with a VANOL-Borate Ester Complex. ACS Omega. 2023, 8, 11588–11595. DOI: 10.1021/acsomega.3c00782.
   PubMed Web of Science ®Google Scholar
• Li, X.; Han, J.; Jones, A. X.; Lei, X. Chiral Boron Complex-Promoted Asymmetric Diels-Alder Cycloaddition and Its Application in Natural Product Synthesis. J. Org. Chem. 2016, 81, 458–468. DOI: 10.1021/acs.joc.5b02248.
   PubMedGoogle Scholar
• Nasir, S. B.; Abd Rahman, N.; Chee, C. F. Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review. COS. 2018, 15, 221–229. DOI: 10.2174/1570179414666170821120234.
   Web of Science ®Google Scholar
• Qi, C.; Xiong, Y.; Eschenbrenner-Lux, V.; Cong, H.; Porco, J. A. Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O. J. Am. Chem. Soc. 2016, 138, 798–801. DOI: 10.1021/jacs.5b12778.
   PubMed Web of Science ®Google Scholar
• Georgieva, M. K.; Santos, A. G. Theoretical Study on Chiral Boron Complex-Promoted Asymmetric Diels-Alder Cycloadditions. Eur. J. Org. Chem. 2022, e202201082, DOI: 10.1002/ejoc.202201082.
   Google Scholar
• Tagra, D.; Bhargava, M.; Agarwal, J. Copper Ferrite Nanoparticles Catalyzed the Challenging Diels-Alder Reaction of Aromatic Chalcones with Cyclopentadiene. Chem. Commun. (Camb) 2023, 59, 11584–11587. DOI: 10.1039/d3cc02290k.
   PubMed Web of Science ®Google Scholar
• Horibe, T.; Ohmura, S.; Katagiri, K.; Ishihara, K. Cationic Iron(III) Salt as an Initiator for Radical Cation-Induced [4 + 2] Cycloaddition. Asian J. Org. Chem. 2020, 9, 395–398. DOI: 10.1002/ajoc.201900749.
   Web of Science ®Google Scholar
• Horibe, T.; Ohmura, S.; Ishihara, K. Structure and Reactivity of Aromatic Radical Cations Generated by FeCl. J. Am. Chem. Soc. 2019, 141, 1877–1881. DOI: 10.1021/jacs.8b12827.
   PubMed Web of Science ®Google Scholar
• Stevenson, S. M.; Higgins, R. F.; Shores, M. P.; Ferreira, E. M. Chromium Photocatalysis: Accessing Structural Complements to Diels-Alder Adducts with Electron-Deficient Dienophiles. Chem. Sci. 2017, 8, 654–660. DOI: 10.1039/c6sc03303b.
   PubMed Web of Science ®Google Scholar
• Liu, Z.; Ganguly, R.; Vidović, D. Pursuing the Active Species in an Aluminium-Based Lewis Acid System for Catalytic Diels-Alder Cycloadditions. Dalton Trans. 2017, 46, 753–759. DOI: 10.1039/c6dt04213a.
   PubMed Web of Science ®Google Scholar
• Ohmura, S.; Katagiri, K.; Kato, H.; Horibe, T.; Miyakawa, S.; Hasegawa, J.-Y.; Ishihara, K. Highly Enantioselective Radical Cation [2 + 2] and [4 + 2] Cycloadditions by Chiral Iron(III) Photoredox Catalysis. J. Am. Chem. Soc. 2023, 145, 15054–15060. DOI: 10.1021/jacs.3c04010.
   PubMed Web of Science ®Google Scholar
• Shaykhutdinova, P.; Oestreich, M. Achieving Enantioselectivity in Difficult Cyclohexa-1,3-Diene Diels-Alder Reactions with Sulfur-Stabilized Silicon Cations as Lewis Acid Catalysts. Org. Lett. 2018, 20, 7029–7033. DOI: 10.1021/acs.orglett.8b02945.
   PubMed Web of Science ®Google Scholar
• Li, Q.; Wong, W. -Y.; Chan, W. -H.; Lee, A. W. M. Second Generation CaSH (Camphor Sulfonyl Hydrazine) Organocatalysis. Asymmetric Diels-Alder Reactions and Isolation of the Catalytic Intermediate. Adv. Synth. Catal. 2010, 352, 2142–2146. DOI: 10.1002/adsc.201000438.
   Web of Science ®Google Scholar
• Mikami, K.; Motoyama, Y.; Terada, M. Asymmetric Catalysis of Diels-Alder Cycloadditions by an Ms-Free Binaphthol-Titanium Complex - Dramatic Effect of Ms, Linear Vs Positive Nonlinear Relationship, and Synthetic Applications. J. Am. Chem. Soc. 1994, 116, 2812–2820. DOI: 10.1021/ja00086a014.
   Web of Science ®Google Scholar
• Mikami, K.; Hong, S. (R)-1,1'-Bi-2,2'-Naphthotitanium Dichloride. 2008. John Wiley & Sons, Ltd. New York.
   Google Scholar
• Bao, H.; Zhou, J.; Wang, Z.; Guo, Y.; You, T.; Ding, K. Insight into the Mechanism of the Asymmetric Ring-Opening Aminolysis of 4,4-Dimethyl-3,5,8-Trioxabicyclo[5.1.0]Octane Catalyzed by Titanium/BINOLate/Water System: Evidence for the Ti(BINOLate)-Bearing Active Catalyst Entities and the Role of Water. J. Am. Chem. Soc. 2008, 130, 10116–10127. DOI: 10.1021/ja801847r.
   PubMed Web of Science ®Google Scholar
• Biancalana, L.; Bortoluzzi, M.; Ferretti, E.; Hayatifar, M.; Marchetti, F.; Pampaloni, G.; Zacchini, S. The Reactions of Alpha-Amino Acids and Alpha-Amino Acid Esters with High Valent Transition Metal Halides: Synthesis of Coordination Complexes, Activation Processes and Stabilization of Alpha-Ammonium Acylchloride Cations. RSC Adv. 2017, 7, 10158–10174. DOI: 10.1039/C7RA00073A.
   Web of Science ®Google Scholar
• Deshpande, S. G.; Jain, S. C. Coordination Compounds of Titanium, Zirconium, Tin, Thorium and Uranium. Indian J. Chem. Sect. A 1990, 29A, 1215.
   Google Scholar
• Jalil, N. S. N.; Hameed, L. T. Schiff Base Complexes of Some Group IV Metal Halides. Phosphorus, Sulfur. Silicon Relat. Elem. 1996, 112, 171–178. DOI: 10.1080/10426509608046360.
   Web of Science ®Google Scholar
• Corbett, J. L.; Weavers, R. T. Aluminosilicate Catalysis of Chalcone Diels-Alder Reactions. Synth. Commun. 2008, 38, 489–498. DOI: 10.1080/00397910701796527.
   Web of Science ®Google Scholar