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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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