Base-Metal Catalysis - presented by Prof. Lingling Chu and Assoc. Prof. Ming Joo Koh and Prof. Zhan Lu and Assoc. Prof. Tatsuhiko Yoshino and Prof. Naohiko Yoshikai

Base-Metal Catalysis

Lingling Chu, Ming Joo Koh, Zhan Lu and Tatsuhiko Yoshino

Prof. Lingling ChuAssoc. Prof. Ming Joo KohAssoc. Prof. Tatsuhiko YoshinoProf. Zhan Lu
Slide at 1:47:23
Synthesis of Pseudo-C2 CCA BnO2C [ref] LiHMDS (1.2 equiv. X 2) HMPA THF, -78 - 0 °C Pd/C, H2 (1 atm) CO2Bn MeOH, 40 °C, 4 h CO2H 84% in 2 steps Br intermediate: Bulman Page, P. C. Org. Biomol. Chem. 2016, 14, 4220.
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References
  • 1.
    P. C. B. Page et al. (2016) New biphenyl iminium salt catalysts for highly enantioselective asymmetric epoxidation: role of additional substitution and dihedral angle. Org. Biomol. Chem.
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Summary (AI generated)

The pseudo C2 chiral carboxylic acids can be synthesized from a di-bromo compound via double addition of acetic acid. The group can then be removed to show the substrate's tosco and various types of bin benty. These oxides are easily accessible, with moderate quality, and substitutions can be made by changing the dioxazolone.