Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

Scholarly Works

• Usman, F. O.; Gogoi, A. R.; Mixdorf, J. C.; Gutierrez, O.; Nguyen, H. M. Rhodium‐Catalyzed Asymmetric Synthesis of 1,2‐Disubstituted Allylic Fluorides. Angewandte Chemie 2023, 135. doi:10.1002/ange.202314843
• Usman, F. O.; Gogoi, A. R.; Mixdorf, J. C.; Gutierrez, O.; Nguyen, H. M. Rhodium-Catalyzed Asymmetric Synthesis of 1,2-Disubstituted Allylic Fluorides. Angewandte Chemie (International ed. in English) 2023, 62, e202314843. doi:10.1002/anie.202314843
• Yan, X.; Li, Z.; Fan, L.; Li, J.; Liu, G. Highly Regio- and Enantioselective Cu/Pd Co-Catalyzed Allylic Alkylation of α-pyridyl-α-fluoroesters: Construction of Quaternary C-F Stereocenters. Chemistry, an Asian journal 2023, 18, e202300160. doi:10.1002/asia.202300160
• Pan, B.-W.; Shi, Y.; Tian, Y.-P.; Zhou, Y.; Zhou, J.; Yu, J.-S. Synthesis of Multifunctional α,α-Difluoroketones through Allylic Alkylation of Difluoroenoxysilanes with MBH Carbonates. Chemistry, an Asian journal 2020, 15, 4028–4032. doi:10.1002/asia.202001145
• Halder, P.; Pol, M. D.; Ahire, M. M.; Mhaske, S. B. Construction of unique SCF3-containing building blocks via allylic alkylation of Morita–Baylis–Hillman adducts. Organic & biomolecular chemistry 2020, 18, 2085–2093. doi:10.1039/d0ob00104j
• Liu, X.; Jin, S.; Zhang, W.; Liu, Q.; Zheng, C.; You, S. Sequence‐Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones. Angewandte Chemie 2019, 132, 2055–2059. doi:10.1002/ange.201912882
• Liu, X.-J.; Jin, S.; Zhang, W.-Y.; Liu, Q.-Q.; Zheng, C.; You, S.-L. Sequence-Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones. Angewandte Chemie (International ed. in English) 2019, 59, 2039–2043. doi:10.1002/anie.201912882
• He, Z.-T.; Jiang, X.; Hartwig, J. F. Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic Pairs by Allylic Substitution with Iridium and Copper Catalysts. Journal of the American Chemical Society 2019, 141, 13066–13073. doi:10.1021/jacs.9b04440
• Zhu, Y.; Mao, Y.; Mei, H.; Pan, Y.; Han, J.; Soloshonok, V. A.; Hayashi, T. Palladium-Catalyzed Asymmetric Allylic Alkylations of Colby Pro-Enolates with MBH Carbonates: Enantioselective Access to Quaternary C-F Oxindoles. Chemistry (Weinheim an der Bergstrasse, Germany) 2018, 24, 8994–8998. doi:10.1002/chem.201801670
• Zhu, Y.; Han, J.; Wang, J.; Shibata, N.; Sodeoka, M.; Soloshonok, V. A.; Coelho, J. A. S.; Toste, F. D. Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs. Chemical reviews 2018, 118, 3887–3964. doi:10.1021/acs.chemrev.7b00778
• Govender, T.; Arvidsson, P. I.; Maguire, G. E. M.; Kruger, H. G.; Naicker, T. Enantioselective Organocatalyzed Transformations of β-Ketoesters. Chemical reviews 2016, 116, 9375–9437. doi:10.1021/acs.chemrev.6b00156
• Sung, H. J.; Mang, J. Y.; Kim, D. Y. Catalytic asymmetric conjugate addition of α-fluoro β-ketophosphonates to nitroalkenes in the presence of nickel complexes. Journal of Fluorine Chemistry 2015, 178, 40–46. doi:10.1016/j.jfluchem.2015.04.021
• Lin, J.-H.; Xiao, J.-C. Recent advances in asymmetric fluorination and fluoroalkylation reactions via organocatalysis. Tetrahedron Letters 2014, 55, 6147–6155. doi:10.1016/j.tetlet.2014.09.031
• Liu, Q.; Qiao, B.; Chin, K. F.; Tan, C.-H.; Jiang, Z. Asymmetric Michael Addition of 5 H‐Oxazol‐4‐ones to Vinyl Sulfones: Stereoselective Synthesis of Monofluorinated Analogs of 2‐Tertiary Hydroxyl‐3‐Methyl‐Substituted Carboxylic Acidl Derivatives. Advanced Synthesis & Catalysis 2014, 356, 3777–3783. doi:10.1002/adsc.201400649
• Chen, W.; Jing, Z.; Chin, K. F.; Qiao, B.; Zhao, Y.; Yan, L.; Tan, C.-H.; Jiang, Z. Catalytic Asymmetric Conjugate Addition of Mercaptans to β-Substituted-β-Trifluoromethyl Oxazolidinone Enoates: Access to Chiral Trifluoromethylated Tertiary Thioethers and Thiols. Advanced Synthesis & Catalysis 2014, 356, 1292–1300. doi:10.1002/adsc.201301027
• Qiao, B.; Liu, Q.; Liu, H.; Yan, L.; Jiang, Z. Asymmetric Decarboxylative 1,4-Addition of Malonic Acid Half Thioesters to Vinyl Sulfones: Highly Enantioselective Synthesis of 3-Monofluoromethyl-3-Arylpropanoic Esters. Chemistry, an Asian journal 2014, 9, 1252–1256. doi:10.1002/asia.201400049
• Qiao, B.; Liu, X.; Duan, S.; Yan, L.; Jiang, Z. Highly enantioselective organocatalytic α-sulfenylation of azlactones. Organic letters 2014, 16, 672–675. doi:10.1021/ol403303k
• Jing, Z.; Liu, J.; Chin, K. F.; Chen, W.; Tan, C.-H.; Jiang, Z. Chiral Bicyclic Guanidine-Catalysed Conjugate Addition of α-Fluoro-β-Ketoesters to Cyclic Enones. Australian Journal of Chemistry 2014, 67, 1119–1123. doi:10.1071/ch14187

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