Turkyilmaz Serhan, Wilcox Craig S
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey.
Tetrahedron Lett. 2017 May 24;58(21):2031-2033. doi: 10.1016/j.tetlet.2017.04.026. Epub 2017 Apr 6.
Sorting tags are oligomeric structures that can be used as protecting groups or chiral auxiliaries enabling solution-phase mixture syntheses of multiple tagged compounds in one pot and allowing for facile and predictable chromatographic separation of products at the end of synthetic sequences. Perfluorinated hydrocarbon and oligomeric ethylene glycol (OEG) derivatives are known classes of sorting tags. Herein we describe the preparation of OEGylated chiral oxazolidinones and their use in asymmetric solution-phase mixture aldol reactions. Through the use of such oxazolidinones based on tyrosine four different individually tagged aldol adducts were obtained as a mixture, chromatographically demixed, detagged, and it was shown that these processes gave the desired aldol products in good yield and enantioselectivity.
分选标签是寡聚结构，可用作保护基团或手性助剂，能够在一锅法中实现多种带标签化合物的溶液相混合合成，并在合成序列结束时便于对产物进行简便且可预测的色谱分离。全氟烃和寡聚乙二醇（OEG）衍生物是已知的分选标签类别。在此，我们描述了OEG化手性恶唑烷酮的制备及其在不对称溶液相混合羟醛反应中的应用。通过使用基于酪氨酸的此类恶唑烷酮，以混合物形式获得了四种不同的单独带标签的羟醛加合物，经色谱分离、去标签处理，结果表明这些过程以良好的产率和对映选择性得到了所需的羟醛产物。
