Siberian Federal University

The interaction of chloromethylallyl ether with carbonyl compounds with metallic zinc in the presence of a chiral ligand, N‑ethyl‑N‑{[(2S)‑pyrrolidin‑2‑yl]methyl}ethanamine, leads to enantioselective synthesis. As a result, unsaturated β‑hydroxyethers are formed in moderate yield and high selectivity. Then, the absolute configuration of the synthesized compounds was determined by the Mosher reagent. The obtained compounds are stable and do not undergo hydrolysis. The reaction duration and the volume of substituents in the alkoxy group do not significantly affect the yield of the target reaction products. The composition of the synthesized compounds contains signals of protons of allyl groups. The reactions and purity of the obtained compounds were monitored by TLC. The structure of the obtained compounds was confirmed by 1H, 13C NMR spectroscopy, and mass spectrometry data. Diastereomeric purities (dp) were determined using chiral phase HPLC analysis. This reaction can also be used to form a C–C bond. Some methylene protons of the synthesized compounds are diastereotopic and appear in the spectra as an AB system. However, we have shown that modulation of the conformational equilibrium in favor of one of the conformers allows a safe assignment of the absolute stereochemistry using only one α‑meth oxytrifluoromethylphenylacetic acid derivative rather than two