Department of Chemistry "Ugo Schiff" (DICUS), University of Florence, Via della Lastruccia 13, Sesto Fiorentino (FI), 50019 Florence, Italy.
Department of Molecular and Translational Medicine (DMMT), University of Brescia, V.le Europa 11 Brescia (BS), 25121 Brescia, Italy.
Molecules. 2022 Feb 9;27(4):1160. doi: 10.3390/molecules27041160.
We have developed an efficient chemical resolution of racemic hydroxy substituted dithia-aza[4]helicenes (DTA[4]H) using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1)-(-)-camphanic acid. Subsequent simple manipulations produced highly optically pure (≥ 99% enantiomeric excess) () and ()- in good yields. The role of the position where the chiral auxiliary is inserted (- vs. ) and the structure of the enantiopure acid used on successful resolution are discussed.
我们开发了一种高效的化学拆分方法，用于拆分外消旋羟基取代的二硫杂氮杂[4]轮烯（DTA[4]H），使用的拆分试剂为手性纯酸。用（1）-（-）-莰烷酸制备的酯可实现更好的非对映选择性分离。随后的简单操作可高产率地得到高光学纯（≥99%对映体过量）（）和（）-。讨论了手性辅助基插入的位置（-与-）和所用手性纯酸的结构对成功拆分的影响。
