Issue Date: November 7, 2011
More Aziridines Now Accessible
A three-component, one-pot strategy gives chemists access to a far broader range of aziridines than previous two-component protocols (Org. Lett., DOI: 10.1021/ol202472z). Chiral aziridines are typically made by combining a preformed imine with a diazo compound using a chiral catalyst. The new one-pot reaction, developed by William D. Wulff and coworkers at Michigan State University, sidesteps the need for making the imine beforehand. Particularly when built from unbranched aliphatic aldehydes, preformed imines can inactivate the aziridination catalyst if used without purification. But purifying such imines can be difficult. Instead, Wulff’s team used its signature chiral boroxinate catalyst to combine an aldehyde, an amine, and a diazo compound all in one go. The strategy yields a variety of aziridines, including ones featuring unbranched aliphatic functionality that could not be accessed using previous two-component methods. The approach could allow chemists to make aziridine-based natural products that feature unbranched aliphatic chains, many of which boast potent antimicrobial properties.
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