A practical and general method for the st©reoselective synthesis of trans-4,5-dis~tituted 2-pyrrolidinones was developed. Hydride reduction of these pyrrolidinones gave the corresponding pyrrolidines.
Synthesis, resolution and absolute configuration of trans 4,5-diphenyl-pyrrolidin-2-one: a possible chiral auxiliary
✍ Scribed by Jaime Escalante; Miguel A. González-Tototzin
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 379 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
b-Lactam (±)-N-benzyl-4-phenyl-azetidin-2-one rac-6a was converted into the g-lactam (±)-trans-4,5-diphenyl-pyrrolidin-2-one rac-5 which was resolved via the preparation of diastereomers with N-phthalyl-L-alanine chloride or D-alanine chloride and its absolute configuration was determined by X-ray crystallographic analysis. This heterocycle has potential as a chiral g-lactam in asymmetric induction due to the steric effects of its phenyl groups.
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