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

…, L Gentilucci, C Tomasini, MPV Castejon-Bordas

Index: Cardillo, Giuliana; Gentilucci, Luca; Tomasini, Claudia; Castejon-Bordas, Maria Pilar Visa Tetrahedron Asymmetry, 1996 , vol. 7, # 3 p. 755 - 762

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Citation Number: 55

Abstract

Benzyl aziridine-2-carboxylates have been obtained in high yield and selectivity by conjugate addition of ammonia to α, β-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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