Conformational rigidity of silicon-stereogenic silanes in asymmetric catalysis: A comparative study

Scholarly Works

• Yan, Y.; Wei, Q.; Su, Z.; Hang, N.-N.; Hayashi, T.; Ming, J. Carbon-silicon-switch effect in enantioselective construction of silicon-stereogenic center from silacyclohexadienones. Nature communications 2024, 15, 9915. doi:10.1038/s41467-024-54241-x
• Han, J. T.; Tsuji, N.; Zhou, H.; Leutzsch, M.; List, B. Organocatalytic asymmetric synthesis of Si-stereogenic silacycles. Nature communications 2024, 15, 5846. doi:10.1038/s41467-024-49988-2
• Landais, Y. Selected Diastereoselective Reactions: Synthesis and Reactivity of Silicon-Stereogenic Silanes. Comprehensive Chirality; Elsevier, 2024; pp 118–137. doi:10.1016/b978-0-32-390644-9.00096-2
• Wang, X.; Feng, C.; Jiang, J.; Maeda, S.; Kubota, K.; Ito, H. Stereospecific synthesis of silicon-stereogenic optically active silylboranes and general synthesis of chiral silyl Anions. Nature communications 2023, 14, 5561. doi:10.1038/s41467-023-41113-z
• Hu, T.; Zhao, C.; Zhang, Y.; Kuang, Y.; Gao, L.; Wang, W.; Su, Z.; Song, Z. Enantioconvergent construction of stereogenic silicon via Lewis base-catalyzed dynamic kinetic silyletherification of racemic chlorosilanes. Nature communications 2023, 14, 4900. doi:10.1038/s41467-023-40558-6
• Zhou, H.; Properzi, R.; Leutzsch, M.; Belanzoni, P.; Bistoni, G.; Tsuji, N.; Han, J. T.; Zhu, C.; List, B. Organocatalytic DYKAT of Si-Stereogenic Silanes. Journal of the American Chemical Society 2023, 145, 4994–5000. doi:10.1021/jacs.3c00858
• Shi, Y.; Shi, X.; Zhang, J.; Qin, Y.; Li, B.; Zhao, D. Sila-spirocyclization involving unstrained C(sp3)-Si bond cleavage. Nature communications 2022, 13, 6697. doi:10.1038/s41467-022-34466-4
• Wang, X.-C.; Li, B.; Ju, C.-W.; Zhao, D. Nickel(0)-catalyzed divergent reactions of silacyclobutanes with internal alkynes. Nature communications 2022, 13, 3392. doi:10.1038/s41467-022-31006-y
• Zhou, H.; Han, J. T.; Nöthling, N.; Lindner, M. M.; Jenniches, J.; Kühn, C.; Tsuji, N.; Zhang, L.; List, B. Organocatalytic Asymmetric Synthesis of Si-Stereogenic Silyl Ethers. Journal of the American Chemical Society 2022, 144, 10156–10161. doi:10.1021/jacs.2c04261
• Chen, S.; Mu, D.; Mai, P.-L.; Ke, J.; Li, Y.; He, C. Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles. Nature communications 2021, 12, 1249. doi:10.1038/s41467-021-21489-6
• Tang, R.-H.; Xu, Z.; Nie, Y.-X.; Xiao, X.-Q.; Yang, K.-F.; Xie, J.-L.; Bin, G.; Yin, G.-W.; Yang, X.-M.; Xu, L.-W. Catalytic Asymmetric trans-Selective Hydrosilylation of Bisalkynes to Access AIE and CPL-Active Silicon-Stereogenic Benzosiloles. iScience 2020, 23, 101268. doi:10.1016/j.isci.2020.101268
• Wu, Y.; Chen, H.; Yang, W.; Fan, Y.; Gao, L.; Su, Z.; Hu, C.; Song, Z. Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon. RSC advances 2019, 9, 26209–26213. doi:10.1039/c9ra05482k
• Xu, L.-W. Chiral Organosilicon Compounds. Organosilicon Compounds; Elsevier, 2017; pp 145–194. doi:10.1016/b978-0-12-801981-8.00004-6
• Xu, L.-W.; Li, L.; Lai, G.; Jiang, J.-X. The recent synthesis and application of silicon-stereogenic silanes: A renewed and significant challenge in asymmetric synthesis. Chemical Society reviews 2010, 40, 1777–1790. doi:10.1039/c0cs00037j
• Rendler, S.; Plefka, O.; Karatas, B.; Auer, G.; Fröhlich, R.; Mück-Lichtenfeld, C.; Grimme, S.; Oestreich, M. Stereoselective alcohol silylation by dehydrogenative Si-O coupling: scope, limitations, and mechanism of the cu-h-catalyzed non-enzymatic kinetic resolution with silicon-stereogenic silanes. Chemistry (Weinheim an der Bergstrasse, Germany) 2008, 14, 11512–11528. doi:10.1002/chem.200801377
• Issenhuth, J. T.; Dagorne, S.; Bellemin-Laponnaz, S. A practical concept for the kinetic resolution of a chiral secondary alcohol based on a polymeric silane. Journal of Molecular Catalysis A: Chemical 2008, 286, 6–10. doi:10.1016/j.molcata.2008.01.046
• Karatas, B.; Rendler, S.; Fröhlich, R.; Oestreich, M. Kinetic resolution of donor-functionalised tertiary alcohols by Cu-H-catalysed stereoselective silylation using a strained silicon-stereogenic silane. Organic & biomolecular chemistry 2008, 6, 1435–1440. doi:10.1039/b802186d
• Klare, H. F. T.; Oestreich, M. Chirale Erkennung mit siliciumstereogenen Silanen: außergewöhnliche Selektivitätsfaktoren bei der kinetischen Racematspaltung von donorfunktionalisierten Alkoholen. Angewandte Chemie 2007, 119, 9496–9499. doi:10.1002/ange.200703847
• Klare, H. F. T.; Oestreich, M. Chiral recognition with silicon-stereogenic silanes: remarkable selectivity factors in the kinetic resolution of donor-functionalized alcohols. Angewandte Chemie (International ed. in English) 2007, 46, 9335–9338. doi:10.1002/anie.200703847

Explore citations to this article at