Flow-Mediated Synthesis of Boc, Fmoc, and Ddiv Monoprotected Diamines

ThingSoon Jong, Mark Bradley*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A series of monoprotected aliphatic diamines (21 examples) were synthesized via continuous flow methods. The carbamates and enamines were obtained in 45-91% yields using a 0.5 mm diameter PTFE tubular flow reactor. Using readily accessible protecting group precursors, the procedure serves as an attractive alternative to existing batch-mode synthetic routes by providing direct, multigram access to N-Boc-, N-Fmoc-, and N-Ddiv-protected compounds with productivity indexes of 1.2-3.6 g/h.

Original languageEnglish
Pages (from-to)422-425
Number of pages4
JournalOrganic letters
Volume17
Issue number3
DOIs
Publication statusPublished - 9 Jan 2015

Keywords

  • SOLID-PHASE SYNTHESIS
  • SYMMETRICAL DIAMINES
  • PEPTIDE-SYNTHESIS
  • PROTECTING GROUP
  • MONOACYLATION
  • POLYAMINES
  • CHEMISTRY
  • EFFICIENT
  • REACTORS

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