✦ LIBER ✦
The intramolecular salt effect in chiral auxiliaries. Enhanced diastereoselectivity in a nitrile oxide cycloaddition via rational transition state stabilization
✍ Scribed by César Raposo; Craig S. Wilcox
- Book ID
- 104260629
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 263 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The use of ion pairs to control a nitrtle oxide cycloaddition is demonstrated. A chiral phenylmaleimide derivative bearing an ionic group and an associated counterion provides enhanced selectivity in the cycloaddition of benzonitrtle oxide. The intramolecular salt effect controls the orientation of the 1,3-dipolar reagent. The nature of the solvent is shown to be relevant in the selectivity of the reaction.