Organic Letters

Intramolecular aziridination: Decomposition of diazoamides with tethered imino bonds

DL Wright, MC McMills

Index: Wright, Dennis L.; McMills, Mark C. Organic Letters, 1999 , vol. 1, # 4 p. 667 - 670

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Citation Number: 20

Abstract

Of three possible mechanistic pathways, tethered oximino ethers react intramolecularly with diazoamides to produce a diazabicyclo [5.1. 0] hexane aziridine containing skeleton. Several acyclic and cyclic templates were synthesized and reacted with rhodium catalysts to prepare their corresponding annulated aziridines. Anomalous behavior was discovered with the piperidine template, resulting in an aziridination occurring during the attempted diazo- ...