Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

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Abstract

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.

Original languageEnglish
Pages (from-to)5265-5267
Number of pages3
JournalChemical Communications
Volume48
Issue number43
DOIs
Publication statusPublished - 2012

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Keywords

  • zincation
  • N-Boc pyrrolidine
  • solvent dependency

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