Akademik Veri Yönetim Sistemi
3rd International Natural Science, Engineering and Material Technologies Conference, Gazimagusa, Kıbrıs (Kktc), 21 - 23 Eylül 2023, ss.87, (Özet Bildiri)
Chiral
diols are structural motifs often found in varied significant natural products
and have also proven precious as chiral ligands and auxiliaries in
stereoselective organic synthesis. Chiral
diols are a useful set of key building blocks for preparing a variety of
important chiral chemicals.1-3
In this study synthesized new chiral
1,3-diols with high enantiomeric purity from new chiral 1,3-keto alcohols with
different configurations. Chiral 1,3-keto alcohols were synthesized by a new
asymmetric aldol method in the first step. This method was developed using a
new proline-derived organocatalyst and Cu(OTf)2 as an additive in
DMSO-H2O for the first time. It was obtained almost >99% ee using
our developed aldol procedure. In the second step, original chiral diols of
high enantiomeric purity were obtained by asymmetric reduction of chiral keto
alcohols with chiral oxazaborolidine reagents. In this way, a two-step asymmetric
reaction was developed for chiral 1,3-diol enantiomers with high enantiomeric
purity.
The structures of all the original chiral
compounds obtained were elucidated by IR, NMR, Mass, and elemental analysis
methods. Their enantiomeric excesses were determined by the chiral HPLC method.