P-chiral 1,7-diphosphanorbornenes: synthesis and application in asymmetric allylic alkylation

References

• Loxq, P.; Manoury, E.; Poli, R.; Deydier, E.; Labande, A. Synthesis of Axially Chiral Biaryl Compounds by Asymmetric Catalytic Reactions with Transition Metals. Coord. Chem. Rev. 2016, 308, 131–190. DOI: 10.1016/j.ccr.2015.07.006.
   Web of Science ®Google Scholar
• Dutartre, M.; Bayardon, J.; Jugé, S. Applications and Stereoselective Syntheses of P-Chirogenic Phosphorus Compounds. Chem. Soc. Rev. 2016, 45, 5771–5794. DOI: 10.1039/c6cs00031b.
   PubMed Web of Science ®Google Scholar
• Xu, G.; Senanayake, C. H.; Tang, W. P-Chiral Phosphorus Ligands Based on a 2,3-Dihydrobenzo[ d][1,3]Oxaphosphole Motif for Asymmetric Catalysis. Acc. Chem. Res. 2019, 52, 1101–1112. DOI: 10.1021/acs.accounts.9b00029.
   PubMed Web of Science ®Google Scholar
• Shet, H.; Parmar, U.; Bhilare, S.; Kapdi, A. R. A Comprehensive Review of Caged Phosphines: synthesis, Catalytic Applications, and Future Perspectives. Org. Chem. Front. 2021, 8, 1599–1656. DOI: 10.1039/D0QO01194K.
   Web of Science ®Google Scholar
• Zagidullin, A. A.; Bezkishko, I. A.; Miluykov, V. A.; Sinyashin, O. G. Phospholes – Development and Recent Advances. Mendeleev Commun 2013, 23, 117–130. DOI: 10.1016/j.mencom.2013.05.001.
   Web of Science ®Google Scholar
• Holz, J.; Gensow, M.-N.; Zayas, O.; Borner, A. Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis. Coc. 2007, 11, 61–106. DOI: 10.2174/138527207779316525.
   Google Scholar
• Jiang, Q.; Xiao, D.; Zhang, Z.; Cao, P.; Zhang, X. Highly Enantioselective Hydrogenation of Cyclic Enol Acetates Catalyzed by a Rh-PennPhos Complex. Angew. Chem. Int. Ed. 1999, 38, 516–518. DOI: 10.1002/(SICI)1521-3773(19990215)38:4<516::AID-ANIE516>3.0.CO;2-B.
   PubMed Web of Science ®Google Scholar
• Breit, B.; Fuchs, E. Chiral Phosphabarrelene Ligands: Synthesis and Evaluation in Rhodium-Catalyzed Asymmetric Hydrogenation. Synthesis. 2006, 13, 2121–2128.DOI: 10.1055/s-2006-942425.
   Google Scholar
• Clochard, M.; Mattmann, E.; Mercier, F.; Ricard, L.; Mathey, F. Phosphinites Derived from the 7-Phosphanorbornene Skeleton: first Results in Asymmetric Catalysis. Org. Lett. 2003, 5, 3093–3094. DOI: 10.1021/ol035067g.
   PubMed Web of Science ®Google Scholar
• Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Synthesis of New Bicyclic P-N Ligands and Their Application in Asymmetric Pd-Catalyzed pi-Allyl Alkylation and Heck Reaction. Org. Lett. 2000, 2, 2885–2888. DOI: 10.1021/ol006323h.
   PubMed Web of Science ®Google Scholar
• Zhi, M.; Gan, Z.; Ma, R.; Cui, H.; Li, E.-Q.; Duan, Z.; Mathey, F. Ag/P-Stereogenic Phosphine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions: A Method to Optically Active Pyrrolidines. Org. Lett. 2019, 21, 3210–3213. DOI: 10.1021/acs.orglett.9b00926.
   PubMed Web of Science ®Google Scholar
• Gan, Z.; Zhi, M.; Han, R.; Li, E.-Q.; Duan, Z.; Mathey, F. P-Stereogenic Phosphines Directed Copper(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions. Org. Lett. 2019, 21, 2782–2785. DOI: 10.1021/acs.orglett.9b00734.
   PubMed Web of Science ®Google Scholar
• Lee, A.; Kim, H. Rhodium-Catalyzed Asymmetric 1,4-Addition of α,β-Unsaturated Imino Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands. J. Am. Chem. Soc. 2015, 137, 11250–11253. DOI: 10.1021/jacs.5b07034.
   PubMed Web of Science ®Google Scholar
• Zagidullin, A. A.; Oshchepkova, E. S.; Chuchelkin, I. V.; Kondrashova, S. A.; Miluykov, V. A.; Latypov, S. K.; Gavrilov, K. N.; Hey-Hawkins, E. P-Chiral 1,7-Diphosphanorbornenes: From Asymmetric phospha-Diels-Alder Reactions towards Applications in Asymmetric Catalysis. Dalton Trans. 2019, 48, 4677–4684. DOI: 10.1039/c9dt00443b.
   PubMed Web of Science ®Google Scholar
• Henry, C. E.; Xu, Q.; Fan, Y. C.; Martin, T. J.; Belding, L.; Dudding, T.; Kwon, O. Hydroxyproline-Derived Pseudoenantiomeric [2.2.1] Bicyclic Phosphines: asymmetric Synthesis of (+)- and (-)-Pyrrolines. J. Am. Chem. Soc. 2014, 136, 11890–11893. DOI: 10.1021/ja505592h.
   PubMed Web of Science ®Google Scholar
• Cai, L.; Zhang, K.; Chen, S.; Lepage, R. J.; Houk, K. N.; Krenske, E. H.; Kwon, O. Catalytic Asymmetric Staudinger-aza-Wittig Reaction for the Synthesis of Heterocyclic Amines. J. Am. Chem. Soc. 2019, 141, 9537–9542. − DOI: 10.1021/jacs.9b04803.
   PubMed Web of Science ®Google Scholar
• Zagidullin, A.; Miluykov, V.; Sinyashin, O.; Hey-Hawkins, E. Сhiral Tricyclic Phosphines Derived from 1-(+)-Neomenthyl-1,2-Diphosphole: Synthesis and Applications in Asymmetric Homogeneous Catalysis. Catal. Today. 2017, 279, 142–146. DOI: 10.1016/j.cattod.2016.06.015.
   Web of Science ®Google Scholar
• Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. BIPNOR: A New, Efficient Bisphosphine Having Two Chiral, Nonracemizable, Bridgehead Phosphorus Centers for Use in Asymmetric Catalysis. Chem. Eur. J. 1997, 3, 1365–1369. DOI: 10.1002/chem.19970030824.
   Web of Science ®Google Scholar
• Zagidullin, A.; Miluykov, V.; Polyancev, F.; Latypov, S.; Sinyashin, O.; Lönnecke, P.; Hey-Hawkins, E. Diastereoselective [4 + 2] Cycloaddition Reaction of 1-Neomenthyl-1,2-Diphosphole: Facile Synthesis of P -Chiral Cage Phosphines. Eur. J. Org. Chem. 2015, 2015, 5326–5329. DOI: 10.1002/ejoc.201500558.
   Web of Science ®Google Scholar
• Oshchepkova, E. S.; Zagidullin, A. A.; Miluykov, V. A.; Sinyashin, O. G. Substituent Effects in the Asymmetric Diels-Alder Cycloaddition of 3,4,5-Triaryl-1-(+)-Neomenthyl-1,2-Diphospholes’ with Maleic Acid Derivatives. Phosphorus Sulfur Silicon. 2016, 191, 1530–1532. DOI: 10.1080/10426507.2016.1212350.
   Web of Science ®Google Scholar
• Zagidullin, A. A.; Ganushevich, Y. S.; Miluykov, V. A.; Lönnecke, P.; Hey-Hawkins, E. Synthesis and Asymmetric [4 + 2] Cycloaddition Reaction of 3,4,5-Triphenyl-1-((1R,2S,5R)-Menthyl)Oxymethyl-1,2-Diphosphole. J. Organomet. Chem. 2020, 914, 121218. DOI: 10.1016/j.jorganchem.2020.121218.
   Web of Science ®Google Scholar
• Zagidullin, A.; Miluykov, V.; Sinyashin, O.; Lönnecke, P.; Hey-Hawkins, E. Cycloadducts of 1-Alkyl-1,2-Diphospholes with N -Phenylmaleimide: Synthesis, Structure, Oxidation, and Thionation Reactions. Heteroatom Chem. 2014, 25, 28–34. DOI: 10.1002/hc.21132.
   Web of Science ®Google Scholar
• Pàmies, O.; Margalef, J.; Cañellas, S.; James, J.; Judge, E.; Guiry, P. J.; Moberg, C.; Bäckvall, J.-E.; Pfaltz, A.; Pericàs, M. A.; Diéguez, M. Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications. Chem. Rev. 2021, 121, 4373–4505. DOI: 10.1021/acs.chemrev.0c00736.
   PubMed Web of Science ®Google Scholar
• Wu, G.; Wu, J.-R.; Huang, Y.; Yang, Y.-W. Enantioselective Synthesis of Quaternary Carbon Stereocenters by Asymmetric Allylic Alkylation: A Review. Chem Asian J. 2021, 16, 1864–1877. DOI: 10.1002/asia.202100432.]
   PubMed Web of Science ®Google Scholar