Aziridinyl carbanion with electron-withdrawing substituent

1 Aziridinyl carbanion with electron-withdrawing substituent 

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Aziridines can also be employed as nucleophiles. When one of the carbon atoms in the aziridine ring is equipped with an electron-withdrawing substituent, these substrates can often be cleanly deprotonated and used for subsequent carbanion chemistry. For example, the anion derived from the trifluoromethyl aziridine 162 engages in nucleophilic addition onto benzaldehyde to give the aziridinyl alcohol 163 in 83% yield <03TL6319>. Similarly, deprotonation of the oxazolinylaziridine 164 followed by treatment with methyl iodide gave mainly the methylated product 165 <03TL2677>. 

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