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Novel Cyclic 1,2‐Diacetals Derived from (2 R, 3 R )‐(+)‐Tartaric Acid: Synthesis and Application as N,O Ligands for the Enantioselective Alkylation of Benzaldehyde by Diethylzinc
Author(s) -
Barros M. Teresa,
Maycock Christopher D.,
Phillips Ana Maria Faísca
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300750
Subject(s) - diethylzinc , chemistry , enantioselective synthesis , benzaldehyde , oxazoline , alkylation , tartaric acid , chelation , alcohol , medicinal chemistry , organic chemistry , stereochemistry , catalysis , citric acid
A chiral cyclic 1,2‐diacetal derived from tartaric acid was used as the basic structural unit for novel ligands. Monooxazoline carbinols in which the degree of substitution of the alcohol and the nature of the stereocentre in the oxazoline ring were varied were synthesized in moderate to good yields. The influence of these structural factors on asymmetric induction was examined in the enantioselective addition of diethylzinc to benzaldehyde. Up to 60% ee was observed with a secondary or a tertiary alcohol as the metal‐chelating group. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)