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Sodium TMP-zincate, [(TMEDA)Na(TMP)((t)Bu)Zn((t)Bu)], can deproto-zincate N-Boc pyrrolidine at ambient temperature in hexane solution, whereas in toluene the captured α-carbanion of the heterocycle attacks the solvent setting off a cascade of reactions that ultimately produce a pyrrolidine-substituted enolate.
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Garden et al. (2012) studied this question.
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