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• W1561503860 abstract "The application of pseudo-enantiomers is of great importance when carbohydratederived chiral tools are used: While d-monosaccharides are easily available from the chiral pool , the corresponding l-enantiomers are mostly expensive and in some cases even unavailable. For the preparation of a pseudo-enantiomer of a given carbohydrate tool, a carbohydrate scaffold with opposite confi guration at relevant stereocenters is chosen. These relevant stereocenters are usually those directly involved in the events determining the direction of the asymmetric induction, that is, the one(s) carrying the substrate (in the case of carbohydrate auxiliaries), coordinating metal centers (in the case of carbohydrate ligands), or shielding one face of a substrate. The remaining stereocenters, which are further from the reacting sites, are neglected and may have any confi guration. Thus the synthesis of a pseudo-enantiomeric tool can start from other l-monosaccharides, which are more readily available, that is, l-rhamnose and l-fucose and even d-carbohydrates may be employed. By this approach the preparation of a real enantiomer from an expensive l-enantiomer of a d-carbohydrate can be avoided altogether. Attractive and powerful as this approach may be it is important to note that choosing suitable a pseudo-enantiomeric auxiliary offering high levels of stereoinduction is by no means trivial. Usually, several tentative pseudo-enantiomers can be envisioned for a given carbohydrate tool but which of them – if any – gives high levels of stereoinduction cannot, unfortunately, be predicted. Therefore, fi nding suitable pseudoenantiomers remains a process of trial and error. With this in view, unsurprisingly, some highly effi cient carbohydrate tools have remained without any suitable pseudo-enantiomer (e.g., the Duthaler–Hafner reagent, Chapter 7)." @default.
• W1561503860 created "2016-06-24" @default.
• W1561503860 creator A5033388737 @default.
• W1561503860 date "2013-01-23" @default.
• W1561503860 modified "2023-09-27" @default.
• W1561503860 title "Reactions of Nucleophiles with Electrophiles Bound to Carbohydrate Auxiliaries" @default.
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• W1561503860 doi "https://doi.org/10.1002/9783527654543.ch1" @default.
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