Diastereoselective synthesis of 3′-unsubstituted N-BOC-aziridine from a readily available chiral α,β-unsaturated imide

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• 作者：Cardillo ; Giuliana ; Gentilucci ; Luca ; Bastardas ; Imma Ratera ; Tolomelli ; Alessandra
• 刊名：Tetrahedron
• 出版年：1998
• 出版时间：July 9, 1998
• 年：1998
• 卷：54
• 期：28
• 页码：8217-8222
• 全文大小：319 K

文摘

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.