Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands
Russian Journal of Organic Chemistry, cilt.56, sa.5, ss.901-909, 2020 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 56 Sayı: 5
- Basım Tarihi: 2020
- Doi Numarası: 10.1134/s1070428020050255
- Dergi Adı: Russian Journal of Organic Chemistry
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
- Sayfa Sayıları: ss.901-909
- Anahtar Kelimeler: 1,2-addition, chiral amino alcohols, enantioselective synthesis, thiolated amino-alcohols
- Hatay Mustafa Kemal Üniversitesi Adresli: Evet
Özet
Abstract: Chiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%) and excellent enantioselectivities (ee up to 99%). The highest enantioselectivity (ee 99%) was obtained with p-trifluorobenzaldehyde as the substrate containing the strongly electron-acceptor CF3 group.