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A comparative study of reactivity and selectivity of chiral diamines and structurally analogous amino alcohol ligands in enantioselective alkylations with diethylzinc
Author(s) -
Silva Serra M. Elisa,
Murtinho Dina,
Rocha Gonsalves A. M. d'A.
Publication year - 2008
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.1428
Subject(s) - chemistry , diethylzinc , enantioselective synthesis , benzaldehyde , alkylation , selectivity , alcohol , diamine , reactivity (psychology) , tartaric acid , organic chemistry , amino acid , stereochemistry , catalysis , biochemistry , medicine , alternative medicine , pathology , citric acid
A series of chiral δ‐diamines and structurally analogous δ‐amino alcohols derived from natural tartaric acid were synthesized and a comparative study of their activity and selectivity in the enantioselective alkylation of aromatic aldehydes was carried out. Our results show that in general the δ‐diamines were found to be better chiral inducers than the corresponding δ‐amino alcohols. The highest selectivity was observed when benzaldehyde was alkylated in the presence of the benzylic diamine, giving ( R )‐1‐phenylpropanol with an ee of 42%. Copyright © 2008 John Wiley & Sons, Ltd.