Legendre Sarah V A-M, Sumby Christopher J, Karton Amir, Greatrex Ben W
School of Science and Technology, University of New England, Armidale 2351, Australia.
Department of Chemistry, School of Physics, Chemistry and Earth Sciences, The University of Adelaide, Adelaide, SA 5000, Australia.
J Org Chem. 2023 Aug 18;88(16):11444-11449. doi: 10.1021/acs.joc.3c00278. Epub 2023 Aug 8.
Bifunctional thiourea/amine organocatalysts have been used for the desymmetrization of -endoperoxides using the Kornblum-DeLaMare reaction, giving 4-hydroxyketones in 78-98% yields with ≤98:2 enantioselectivity. The influence of the catalyst structure, solvent, and temperature was examined. The most promising catalyst was applied to the kinetic resolution of racemic endoperoxides to give enantioenriched materials (≤99:1 er).
双功能硫脲/胺有机催化剂已被用于利用科恩布卢姆-德拉马尔反应对内过氧化物进行去对称化反应，以78 - 98%的产率得到4-羟基酮，对映选择性≤98:2。研究了催化剂结构、溶剂和温度的影响。将最有前景的催化剂应用于外消旋内过氧化物的动力学拆分，以得到对映体富集的产物（对映体过量值≤99:1）。
