Phase transfer catalyzed aziridination of alpha-bromo-2-cyclopenten-1-one

作者：Mekonnen A; Carlson R^*

来源：Tetrahedron, 2006, 62(5): 852-856.

DOI：10.1016/j.tet.2005.10.060

• aziridination
• phase transfer catalysis
• primary aliphatic amines
• conjugate addition-imitated ring closure reaction
• bicyclic-alpha-keto-aziridines

An efficient and highly selective synthesis of bicyclic-alpha-keto aziridines from 2-bromo-2-cyclopentenone and aliphatic primary amines mediated by phase transfer catalysts (PTCs) in water at room temperature is demonstrated. Bicyclic-alpha-keto-aziridines are highly strained and reactive compounds that can be used in the synthesis of biologically active compounds. Therefore, the present strategy with its mild reaction conditions opens up a new entry to the synthesis of unusual aziridines using inexpensive reagents.

• 出版日期2006-1-30