Intramolecular metalloamination of N,N-dimethylhydrazinoalkenes: A versatile method to access functionalized piperidines and pyrrolidines

Bryce G Sunsdahl, Adrian R. Smith, Tom Livinghouse

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Highly diastereoselective metalloamination/cyclization reactions of zinc(II) hydrazides obtained through reaction of diethylzinc with N,N-dimethylhydrazinoalkenes are described.The resulting organozinc intermediates undergo facile allylation and acylation, in situ, to provide the corresponding functionalized piperidines and pyrrolidines.

Original languageEnglish (US)
Pages (from-to)14352-14356
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number52
DOIs
StatePublished - Dec 22 2014

Keywords

  • Cyclization
  • Hydrazines
  • Metalloamination
  • Nitrogen heterocycles
  • Organozinc compounds

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