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Cite the Following Article
Asymmetric desymmetrization of meso-diols by C2-symmetric chiral 4-pyrrolidinopyridines
Hartmut Schedel, Keizo Kan, Yoshihiro Ueda, Kenji Mishiro, Keisuke Yoshida, Takumi Furuta and Takeo Kawabata
Beilstein J. Org. Chem. 2012, 8, 1778–1787.
https://doi.org/10.3762/bjoc.8.203
How to Cite
Schedel, H.; Kan, K.; Ueda, Y.; Mishiro, K.; Yoshida, K.; Furuta, T.; Kawabata, T. Beilstein J. Org. Chem. 2012, 8, 1778–1787. doi:10.3762/bjoc.8.203
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- Imayoshi, A. Introduction. Springer Theses; Springer Singapore, 2021; pp 1–6. doi:10.1007/978-981-16-7431-0_1
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- Metrano, A. J.; Chinn, A. J.; Shugrue, C. R.; Stone, E. A.; Kim, B.; Miller, S. J. Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms. Chemical reviews 2020, 120, 11479–11615. doi:10.1021/acs.chemrev.0c00523
- Li, J.; Grosslight, S.; Miller, S. J.; Sigman, M. S.; Toste, F. D. Site-Selective Acylation of Natural Products with BINOL-Derived Phosphoric Acids. ACS catalysis 2019, 9, 9794–9799. doi:10.1021/acscatal.9b03535
- Suzuki, T. Recent Advances in the Desymmetrization of meso-Diols. Journal of Synthetic Organic Chemistry, Japan 2018, 76, 810–819. doi:10.5059/yukigoseikyokaishi.76.810
- Suzuki, T. Recent topics in the desymmetrization of meso-diols. Tetrahedron Letters 2017, 58, 4731–4739. doi:10.1016/j.tetlet.2017.10.048
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