Synthesis of novel thiophene-based chiral ligands and their application in asymmetric Henry reaction
Applied Organometallic Chemistry, vol.27, no.5, pp.283-289, 2013 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 27 Issue: 5
- Publication Date: 2013
- Doi Number: 10.1002/aoc.2969
- Journal Name: Applied Organometallic Chemistry
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.283-289
- Keywords: chiral amino alcohols, copper complex, enantioselective synthesis, Henry reaction, thiolated amino alcohols
- Hatay Mustafa Kemal University Affiliated: Yes
Abstract
Novel chiral thiolated amino alcohols were synthesized from norephedrine and thiophene carbaldehydes (methyl- or ethyl-substituted) and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide β-hydroxy nitroalkanols in high conversion (92%). The reaction was optimized in terms of the metal, solvent, temperature and amount of chiral ligand. The corresponding catalyst with Cu(OTf)2 and 2-propanol as the solvent provided the best enantioselectivities (up to 96% ee) of the corresponding nitroalcohols for aliphatic aldehydes. Copyright © 2013 John Wiley & Sons, Ltd. Chiral thiophene contanining amino alcohol ligands were synthesized from norephedrine and substituted 5-thiophene-2-carbaldehyde. This novel chiral ligands were used to catalyze enantioselective Henry reaction of various aldehydes and nitroalkanes in high yields with good to high enantio- and diastereoselectivities. Copyright © 2013 John Wiley & Sons, Ltd.