Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

Teemu Yrjö Manuel Niemi, Israel Fernández, Bethany Steadman, Jere Kristian Mannisto, Timo Juhani Repo

Research output: Contribution to journalArticleScientificpeer-review

Abstract

We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.
Original languageEnglish
JournalChemical Communications
Volume54
Issue number25
Pages (from-to)3166-3169
Number of pages4
ISSN1359-7345
DOIs
Publication statusPublished - 28 Mar 2018
MoE publication typeA1 Journal article-refereed

Fields of Science

  • 116 Chemical sciences
  • ATMOSPHERIC-PRESSURE
  • CARBOXYLATIVE CYCLIZATION
  • CO2
  • 2-OXAZOLIDINONES
  • URETHANES
  • CONVERSION
  • FIXATION
  • OXAZOLIDIN-2-ONES
  • ORGANOCATALYST
  • AZIRIDINES

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