Facile direct synthesis of unsymmetrical ureas from N-Alloc-, N-Cbz-, and N-Boc-protected amines using DABAL-Me3

Soosung Kang, Hee Kwon Kim

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A practical synthetic method for the direct synthesis of unsymmetrically substituted ureas from N-Alloc-, N-Cbz-, and N-Boc-protected amines is described. In this study, efficient direct conversion of the Alloc-, Cbz-, and Boc-carbamate compounds to ureas was achieved in the presence of DABAL-Me3, an air stable and easily handled reagent. Using this reaction method, both protected aromatic and aliphatic amines were successfully transformed into various trisubstituted and tetrasubstituted ureas with high yields without side product. Our findings offer promising guidelines for direct preparation of useful ureas from N-Alloc-, N-Cbz-, and N-Boc-carbamates.

Original languageEnglish
Pages (from-to)4036-4046
Number of pages11
JournalTetrahedron
Volume74
Issue number30
DOIs
StatePublished - 26 Jul 2018

Keywords

  • DABAL-Me
  • Protected carbamates
  • Unsymmetrical ureas
  • Urea synthesis

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