An investigation of the binding of (S)-monothioBINOLate to rare earth metal cations

References

• Jacobson, E. N.; Andreas, P.; Yamamoto, H. Comprehensive Asymmetric Catalysis. Springer: New York, 1999.
   Google Scholar
• Walsh, P. J.; Kozlowski, M. C. Fundamentals of Asymmetric Catalysis. University Science Books: Sausalito, CA, 2008.
   Google Scholar
• Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W. L. Rare-Earth Metal Triflates in Organic Synthesis. Chem. Rev. 2002, 102, 2227–2302.
   PubMed Web of Science ®Google Scholar
• Martin, M.; El Hellani, A.; Yang, J.; Collin, J.; Bezzenine-Lafollée, S. Synthesis of Rare Earth Catalysts and Their Applications for Enantioselective Synthesis of Heterocyclic β-Amino Alcohols. J. Org. Chem. 2011, 76, 9801–9808. DOI: 10.1002/chin.201213132.
   PubMed Web of Science ®Google Scholar
• Hu, L.; Lu, C.; Zhao, B.; Yao, Y. Intermolecular Addition of Alcohols to Carbodiimides Catalyzed by Rare-Earth Metal Amides. Org. Chem. Front. 2018, 5, 905–908. DOI: 10.1039/C7QO00991G.
   Web of Science ®Google Scholar
• Guan, B.-T.; Hou, Z. Rare-Earth-Catalyzed C-H bond addition of pyridines to olefins. J. Am. Chem. Soc. 2011, 133, 18086–18089. DOI: 10.1021/ja208129t.
   PubMed Web of Science ®Google Scholar
• Luo, Y.; Teng, H.-L.; Nishiura, M.; Hou, Z. Asymmetric Yttrium-Catalyzed C(sp3)−H Addition of 2-Methyl Azaarenes to Cyclopropenes. Angew. Chem. Int. Ed. 2017, 56, 9207–9210. DOI: 10.1002/anie.201705431.
   PubMed Web of Science ®Google Scholar
• Kumagai, N.; Kanai, M.; Sasai, H. A Career in Catalysis: Masakatsu Shibasaki. ACS Catal. 2016, 6, 4699–4709. DOI: 10.1021/acscatal.6b01227.
   Web of Science ®Google Scholar
• Gröger, H. Shibasaki Catalysts and Their Use for Asymmetric Synthetic Applications by the Chemical Industry. Eur. J. Org. Chem. 2016, 2016, 4116–4123. DOI: 10.1002/ejoc.201600174.
   Web of Science ®Google Scholar
• Matsunaga, S.; Shibasaki, M. Recent Advances in Cooperative Bimetallic Asymmetric Catalysis: dinuclear Schiff Base Complexes. Chem. Commun. 2014, 50, 1044–1057. DOI: 10.1039/C3CC47587E.
   PubMed Web of Science ®Google Scholar
• Robinson, J. R.; Gu, J.; Carroll, P. J.; Schelter, E. J.; Walsh, P. J. Exchange Processes in Shibasaki’s Rare Earth Alkali Metal BINOLate Frameworks and Their Relevance in Multifunctional Asymmetric Catalysis. J. Am. Chem. Soc. 2015, 137, 7135–7144. DOI: 10.1021/jacs.5b02201.
   PubMed Web of Science ®Google Scholar
• Robinson Jerome, R.; Carroll Patrick, J.; Walsh Patrick, J.; Schelter Eric, J. The Impact of Ligand Reorganization on Cerium(III) Oxidation Chemistry. Angew. Chem. Int. Ed. 2012, 51, 10159–10163. DOI: 10.1002/anie.201203481.
   PubMed Web of Science ®Google Scholar
• Robinson, J. R.; Carroll, P. J.; Walsh, P. J.; Schelter, E. J. Uranium(IV) BINOLate Heterobimetallics: Synthesis and Reactivity in an Asymmetric Diels–Alder Reaction. Organometallics 2013, 32, 1493–1499. DOI: 10.1021/om3011849.
   Web of Science ®Google Scholar
• Robinson, J. R.; Fan, X.; Yadav, J.; Carroll, P. J.; Wooten, A. J.; Pericàs, M. A.; Schelter, E. J.; Walsh, P. J. Air- and Water-Tolerant Rare Earth Guanidinium BINOLate Complexes as Practical Precatalysts in Multifunctional Asymmetric Catalysis. J. Am. Chem. Soc. 2014, 136, 8034–8041. DOI: 10.1021/ja502568g.
   PubMed Web of Science ®Google Scholar
• Robinson, J. R.; Gordon, Z.; Booth, C. H.; Carroll, P. J.; Walsh, P. J.; Schelter, E. J. Tuning Reactivity and Electronic Properties through Ligand Reorganization within a Cerium Heterobimetallic Framework. J. Am. Chem. Soc. 2013, 135, 19016–19024. DOI: 10.1021/ja410688w.
   PubMed Web of Science ®Google Scholar
• Nieto, I.; Wooten, A. J.; Robinson, J. R.; Carroll, P. J.; Schelter, E. J.; Walsh, P. J. Synthesis and Catalytic Activity of Heterobimetallic Rare Earth–Zinc Ethyl BINOLate Analogues of Shibasaki’s Catalysts. Organometallics 2013, 32, 7431–7439. DOI: 10.1021/om4009444.
   Google Scholar
• Panetti, G. B.; Robinson, J. R.; Carroll, P. J.; Gau, M. R.; Manor, B. C.; Walsh, P. J.; Schelter, E. J. Synthesis of Novel Copper-Rare Earth BINOLate Frameworks from a Hydrogen Bonding DBU-H Rare Earth BINOLate Complex. Dalton Trans. 2018, 47, 14408–14410. DOI: 10.1039/C8DT03335H.
   PubMed Web of Science ®Google Scholar
• Azad, S. M.; Bennett, S. M. W.; Brown, S. M.; Green, J.; Sinn, E.; Topping, C. M.; Woodward, S. Catalytic Conjugate Addition Promoted by the Copper(I)–Monothiobinaphthol System. Part 2.1 Optimal Ligand Synthesis and Initial Catalytic Results. J. Chem. Soc, Perkin Trans. 1 1997, 687–694. DOI: 10.1039/a605620b.
   Google Scholar
• Bennett, S. M. W.; Brown, S. M.; Conole, G.; Dennis, M. R.; Fraser, P. K.; Radojevic, S.; McPartlin, M.; Topping, C. M.; Woodward, S. Catalytic Conjugate Addition Promoted by the Copper(I)-Monothiobinaphthol System. Part 3. Comparison of Three Thiolate-Based Catalytic Systems. J. Chem. Soc, Perkin Trans. 1 1999, 3127–3132. DOI: 10.1039/a906373k.
   Google Scholar
• Fraser, P. K.; Woodward, S. Highly Enantioselective Conjugate Addition of AlMe3 to Linear Aliphatic Enones by a Designed Catalyst. Chem. Eur. J. 2003, 9, 776–783. DOI: 10.1002/chem.200390087.
   PubMed Web of Science ®Google Scholar
• Dennis, M. R.; Woodward, S. Enantiopure 3-Amido or 3,3′-Bisamido Substituted 1,1′-bi-2-Naphthols by Anionic Fries Rearrangements. J. Chem. Soc, Perkin Trans. 1 1998, 1081–1086. DOI: 10.1039/a708436f.
   Google Scholar
• Bradley, D. C.; Ghotra, J. S.; Hart, F. A. Low Co-Ordination Numbers in Lanthanide and Actinide Compounds. Part I. The Preparation and Characterization of Tris{Bis(Trimethylsilyl)-Amido}Lanthanides. J. Chem. Soc, Dalton Trans. 1973, 1021–1023. DOI: 10.1039/dt9730001021.
   Google Scholar