Beaufour M, Merelli B, Menguy L, Cherton J-C
Université de Versailles, Laboratoire SIRCOB (Institut UPRESA CNRS 8086), Département de Chimie, Versailles, France.
Chirality. 2003 May 15;15(5):382-90. doi: 10.1002/chir.10225.
Studies of the perturbing effect of chiral solvating agents (CSAs) 5a and mostly of 5c upon the NMR spectra of chiral Delta(2)-oxazoline 1 demonstrated the ability of these fluoroalcohols to afford diastereomeric solvates from these solutes. Thus, for all tested Delta(2)-oxazolines 1Aa-d, 1Ba, and 1e there is at least one possibility to proceed to their enantiomeric discrimination either by (1)H or (19)F NMR using these CSAs (see Fig. 1). NMR results are discussed from substrate and CSA structure standpoints and a solvation model is proposed on the basis of the inequivalence senses generally observed. Then the method was applied to extracts of incubated locust tissues obtained by solid phase extraction (SPE) after a partial unmasking of the substrate 1.
对手性溶剂化剂（CSA）5a以及主要是5c对手性Δ²-恶唑啉1的核磁共振谱的扰动效应研究表明，这些氟代醇能够与这些溶质形成非对映体溶剂化物。因此，对于所有测试的Δ²-恶唑啉1Aa-d、1Ba和1e，使用这些CSA通过¹H或¹⁹F核磁共振至少有一种方法可以进行对映体鉴别（见图1）。从底物和CSA结构的角度讨论了核磁共振结果，并基于普遍观察到的不等效意义提出了一种溶剂化模型。然后将该方法应用于经部分底物1去掩蔽后通过固相萃取（SPE）获得的孵化蝗虫组织提取物。
