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Synthesis of enantiomerically pure trans aziridine-2-carboxylates by diastereoselective Gabriel-cromwell reaction

โœ Scribed by Giuliana Cardillo; Luca Gentilucci; Claudia Tomasini; Maria Pilar Visa Castejon-Bordas

Book ID
103977433
Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
487 KB
Volume
7
Category
Article
ISSN
0957-4166

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โœฆ Synopsis

Benzyl aziridine-2-carboxylates have been obtained in high yield and selectivity by conjugate addition of ammonia to ct,13-unsaturated chiral imides followed by treatment with lithium benzyloxide. A ring-expansion of the aziridine to an oxazoline allowed the determination of the absolute stereochemistry for the newly formed stereogenic centres.

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