使用双功能有机催化剂对内过氧化物进行去对称化和动力学拆分
Desymmetrization and Kinetic Resolution of Endoperoxides Using a Bifunctional Organocatalyst.
作者信息
Legendre Sarah V A-M, Sumby Christopher J, Karton Amir, Greatrex Ben W
机构信息
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.
出版信息
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）。
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