Literature DB >> 29528063

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

Teemu Niemi1, Israel Fernández2, Bethany Steadman1, Jere K Mannisto1, Timo Repo1.   

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.

Entities:  

Year:  2018        PMID: 29528063     DOI: 10.1039/c8cc00636a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  3 in total

1.  Solid-phase synthesis of D-fructose-derived Heyns peptides utilizing Nα-Fmoc-Lysin[Nε-(2-deoxy-D-glucos-2-yl),Nε-Boc]-OH as building block.

Authors:  Sebastian Schmutzler; Daniel Knappe; Andreas Marx; Ralf Hoffmann
Journal:  Amino Acids       Date:  2021-05-02       Impact factor: 3.520

2.  Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones.

Authors:  Shumei Xia; Yu Song; Xuedong Li; Hongru Li; Liang-Nian He
Journal:  Molecules       Date:  2018-11-20       Impact factor: 4.411

3.  CO2 Methanation via Amino Alcohol Relay Molecules Employing a Ruthenium Nanoparticle/Metal Organic Framework Catalyst.

Authors:  Xinjiang Cui; Serhii Shyshkanov; Tu N Nguyen; Arunraj Chidambaram; Zhaofu Fei; Kyriakos C Stylianou; Paul J Dyson
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-10       Impact factor: 15.336

  3 in total

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