Straightforward deprotonation of soluble tetramethylammonium salts with alkyllithium reagents gives lithiomethyl trimethylammonium reagents. Coordination of the Li cation is crucial to the stability of these ‘N–C ylides’. These reagents were used to prepare epoxides, aziridines and allylic alcohols.
The article was received on 16 Jun 2014, accepted on 17 Jul 2014 and first published on 30 Jul 2014
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