Tetrahedron p. 8217 - 8222 (1998)
Update date:2022-07-29
Topics:
Cardillo, Giuliana
Gentilucci, Luca
Bastardas, Imma Ratera
Tolomelli, Alessandra
The conjugate addition of N-BOC-O-benzoyl hydroxylamine catalysed by sodium hydride to a chiral α,β-unsaturated imide gives a 3'-(BOC benzoyloxyaminopropanoyl) derivative. This undergoes cyclization upon treatment with sodium or lithium bases to give a 3'-unsubstituted N-BOC aziridine-2-imide in good yield and diastereoselectivity. When N-BOC-O-benzoyl hydroxylamine is deprotonated with stoichiometric lithium or sodium bases, the intermediate enolate resulting from the 1,4-addition spontaneously undergoes cyclization affording in a single step the N-BOC aziridine in higher yield.
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(1998)
