Department of Chemistry, University of Helsinki, A.I. Virtasenaukio 1, 00014 Helsinki, Finland.
J Org Chem. 2020 May 1;85(9):5799-5806. doi: 10.1021/acs.joc.9b03320. Epub 2020 Mar 10.
Herein we report a unique method for preparing diaryl hydroxyl dicarboxylic acids in a diastereospecific manner. The three-component reaction occurs between amino acid, aromatic aldehyde, and primary alcohol in alkaline solutions under microwave-assisted conditions. The dicarboxylic acids are isolated as sodium salts in high yields (up to 77%) by direct precipitation from the reaction solution. The experimental results suggest that the diastereospecificity originates from a [3,3]-sigmatropic rearrangement followed by a sodium-assisted hydride transfer. As further shown, the previously unreported dicarboxylic acids are easily turned into corresponding δ-lactones.
在此，我们报告了一种独特的方法，以非对映选择性方式制备二芳基羟基二羧酸。在微波辅助条件下，氨基酸、芳香醛和伯醇在碱性溶液中发生三组分反应。通过直接从反应溶液中沉淀，将二羧酸以高收率（高达 77%）分离为钠盐。实验结果表明，非对映选择性源于[3,3]-σ重排，随后是钠辅助的氢转移。进一步表明，以前未报道的二羧酸很容易转化为相应的δ-内酰胺。
