Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1349148 | Tetrahedron: Asymmetry | 2005 | 5 Pages |
Abstract
The basic reagent vinyloxyethoxy titanium trisisopropyloxide, easily modified by replacing two of the isopropyloxides with the optically active diol (R)- or (S)-BINOL, reacts with simple, prochiral aldehydes to give chiral β-hydroxy-1,3-dioxolanes with enantiomeric ratios up to 99:1. The same reagents, (R)- or (S)-configured, react with the chiral 2,3-O-isopropylidene-d-glyceraldehyde to give the corresponding open chain pentose derivatives. The main components have opposite descriptors at the newly created stereogenic center, indicating strong reagent control. A comparable system, modified by (R,R)- or (S,S)-TADDOL shows a weaker induction with the chiral aldehyde, but now with the same product configuration for both reagents, indicating predominant substrate control.
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Authors
Peter Maier, Hartmut Redlich, Jessica Richter,