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Cite the Following Article
Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives
Martina Bonsignore, Maurizio Benaglia, Laura Raimondi, Manuel Orlandi and Giuseppe Celentano
Beilstein J. Org. Chem. 2013, 9, 633–640.
https://doi.org/10.3762/bjoc.9.71
How to Cite
Bonsignore, M.; Benaglia, M.; Raimondi, L.; Orlandi, M.; Celentano, G. Beilstein J. Org. Chem. 2013, 9, 633–640. doi:10.3762/bjoc.9.71
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- Feng, X.; Du, H. Reduction Hydrosilylation of C=O and C=N. Comprehensive Chirality; Elsevier, 2024; pp 431–483. doi:10.1016/b978-0-32-390644-9.00042-1
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- Chen, W.; Tan, C.-H.; Wang, H.; Ye, X. The Development of Organocatalytic Asymmetric Reduction of Carbonyls and Imines Using Silicon Hydrides. European Journal of Organic Chemistry 2021, 2021, 3091–3112. doi:10.1002/ejoc.202100394
- Triandafillidi, I.; Voutyritsa, E.; Kokotos, C. G. Recent advances in reactions promoted by amino acids and oligopeptides. Physical Sciences Reviews 2020, 5, 29–84. doi:10.1515/psr-2018-0086
- Hasdemir, B.; Yaşa, H.; Yıldız, T.; Küçük, H. B.; Onar, H. Ç. Asymmetric Synthesis of Chiral γ‐ and δ‐Amino Esters Using Trichlorosilane Activated with a Lewis Base Catalyst. ChemistrySelect 2020, 5, 6035–6039. doi:10.1002/slct.202000790
- Zhao, B.; Shang, R.; Wang, G.-Z.; Wang, S.; Chen, H.; Fu, Y. Palladium-Catalyzed Dual Ligand-Enabled Alkylation of Silyl Enol Ether and Enamide under Irradiation: Scope, Mechanism, and Theoretical Elucidation of Hybrid Alkyl Pd(I)-Radical Species. ACS Catalysis 2019, 10, 1334–1343. doi:10.1021/acscatal.9b04699
- Rossi, S.; Denmark, S. E. Organosilicon Chemistry; Wiley, 2019; pp 333–415. doi:10.1002/9783527814787.ch10
- Sugiura, M.; Ashikari, Y.; Takahashi, Y.; Yamaguchi, K.; Kotani, S.; Nakajima, M. Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/ Z-Isomerization, Regioselectivity, and Synthetic Applications. The Journal of organic chemistry 2019, 84, 11458–11473. doi:10.1021/acs.joc.9b01298
- Li, S.; Wang, J.; Xia, P.-J.; Zhao, Q.-L.; Wang, C.-M.; Xiao, J.-A.; Chen, X.; Xiang, H.-Y.; Yang, H. Organocatalytic Domino Entry to an Octahydroacridine Scaffold Bearing Three Contiguous Stereocenters. The Journal of organic chemistry 2018, 83, 12284–12290. doi:10.1021/acs.joc.8b01875
- Salomó, E.; Rojo, P.; Hernández-Lladó, P.; Riera, A.; Verdaguer, X. P-Stereogenic and Non-P-Stereogenic Ir-MaxPHOX in the asymmetric hydrogenation of N-Aryl imines. Isolation and X-ray analysis of imine iridacycles. The Journal of organic chemistry 2018, 83, 4618–4627. doi:10.1021/acs.joc.8b00361
- Min, C.; Seidel, D. Asymmetric Brønsted acid catalysis with chiral carboxylic acids. Chemical Society reviews 2017, 46, 5889–5902. doi:10.1039/c6cs00239k
- Brenna, D.; Massolo, E.; Puglisi, A.; Rossi, S.; Celentano, G.; Benaglia, M.; Capriati, V. Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents. Beilstein journal of organic chemistry 2016, 12, 2620–2626. doi:10.3762/bjoc.12.258
- Kocovsky, P.; Malkov, A. V. Lewis Base Catalysis in Organic Synthesis - Lewis bases as catalysts in the reduction of imines and ketones with silanes (n → σ*). Lewis Base Catalysis in Organic Synthesis; Wiley, 2016; pp 1077–1112. doi:10.1002/9783527675142.ch22
- Barrulas, P.; Genoni, A.; Benaglia, M.; Burke, A. J. Cinchona‐Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation. European Journal of Organic Chemistry 2014, 2014, 7339–7342. doi:10.1002/ejoc.201403180
- Hu, X.-Y.; Zhang, M.; Shu, C.; Zhang, Y.; Liao, L.-H.; Yuan, W.-C.; Zhang, X.-M. Enantioselective Lewis-Base-Catalyzed Asymmetric Hydrosilylation of Substituted Benzophenone N-Aryl Imines: Efficient Synthesis of Chiral (Diarylmethyl)amines. Advanced Synthesis & Catalysis 2014, 356, 3539–3544. doi:10.1002/adsc.201400643
- Barrulas, P.; Benaglia, M.; Burke, A. J. Synthesis of novel cinchona-amino acid hybrid organocatalysts for asymmetric catalysis. Tetrahedron: Asymmetry 2014, 25, 923–935. doi:10.1016/j.tetasy.2014.05.003
- Rossi, S.; Benaglia, M.; Massolo, E.; Raimondi, L. Organocatalytic strategies for enantioselective metal-free reductions. Catalysis Science & Technology 2014, 4, 2708–2723. doi:10.1039/c4cy00033a
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- BURKE ANTHONY; CAMBEIRO BARRULAS PEDRO MIGUEL. Picolinamide-cinchona organocatalysts and derivatives. US 9844773 B2, Dec 19, 2017.
- BURKE ANTHONY; CAMBEIRO BARRULAS PEDRO MIGUEL. NOVEL PICOLINAMIDE-CINCHONA ORGANOCATALYSTS AND DERIVATIVES. WO 2015052656 A1, April 16, 2015.