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