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Salicylaldehyde based oxazolidines as catalysts for the asymmetric addition of diethylzinc to aldehydes
Author(s) -
Parrott Raleigh W.,
Hamaker Christopher G.,
Hitchcock Shawn R.
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450336
Subject(s) - diethylzinc , chemistry , oxazolidine , salicylaldehyde , yield (engineering) , ephedrine , catalysis , condensation , organic chemistry , isopropyl , derivative (finance) , stereochemistry , enantioselective synthesis , schiff base , materials science , thermodynamics , physics , neuroscience , economics , financial economics , metallurgy , biology
A series of oxazolidines have been prepared by condensation of N‐ isopropyl norephedrine with a variety of salicylaldehyde derivatives. Despite the stereochemical relationship of (1 R ,2 S )‐norephedrine with (1 R ,2 S )‐ephedrine, the resultant oxazolidines 12‐14 were determined to have a stronger stereochemical relationship with (1 S ,2 S )‐pseudoephedrine based oxazolidines. The resultant oxazolidines were used as catalytic ligands in the addition of diethylzinc to several aldehydes. It was determined that the oxazolidine derivative 12 gave the highest yield and a moderate enantioselectivity.