2-吗啉醇盐酸盐的手性合成及晶体结构

Synthesis and Crystal Structure of Chiral 2-Morpholinol Hydrochloride

以单一手性纯试剂与外消旋体化合物反应,合成了4对手性纯化合物(2R,3R,5S)-2-吗啉醇盐酸盐及其对映体(2S,3S,5R)-2-吗啉醇盐酸盐。其结构经IR、1HNMR、13CNMR及ESI-MS表征,利用X-射线单晶衍射法测定了其中一对对映体的空间构型。利用吗啉六元环椅式构象比船式构象稳定的特性,系统探讨了以构象稳定性促进目标化合物构型形成的手性化合物合成机制及规律,为手性化合物合成方法提供了新启示。

Four pairs of chiral compounds（ 2 R,3 R,5 S）-2-morpholinol hydrochloride and their enantiomers（ 2 S,3 S,5 R）-2-morpholinol hydrochloride were synthesized by the chiral reagents with raceme compounds. The structures were confirmed by IR,1 HNMR,13 CNMR and ESI-MS. The crystal structures of enantiomer were determined by X-ray single-crystal diffraction analysis The mechanism and regularity of the synthesis of chiral morpholinol compounds were investigated by means of the higher stability of chair conformation that of boat conformation,which facilitate the formation of the target compound steric configuration.This provides a new enlightenment for the study of the synthesis of chiral compounds.