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Synthesis of novel thiophene‐based chiral ligands and their application in asymmetric Henry reaction
Author(s) -
Ebru Aydin A.
Publication year - 2013
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.2969
Subject(s) - nitromethane , chemistry , nitroaldol reaction , catalysis , thiophene , solvent , chiral ligand , ligand (biochemistry) , organic chemistry , combinatorial chemistry , enantioselective synthesis , biochemistry , receptor
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.