Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide

Tadashi Ema, Maki Yokoyama, Sagiri Watanabe, Sota Sasaki, Hiromi Ota, Kazuto Takaishi

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of epoxides. A catalytic cycle proposed was supported by DFT calculations.

Original languageEnglish
Pages (from-to)4070-4073
Number of pages4
JournalOrganic Letters
Volume19
Issue number15
DOIs
Publication statusPublished - Aug 4 2017

Fingerprint

epoxy compounds
Epoxy Compounds
Carbon Dioxide
carbon dioxide
Kinetics
Carbonates
kinetics
Hydrogen Bonding
Discrete Fourier transforms
carbonates
Hydrogen bonds
Crystal structure
Chemical activation
X-Rays
activation
X rays
cavities
cycles
crystal structure
hydrogen

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide. / Ema, Tadashi; Yokoyama, Maki; Watanabe, Sagiri; Sasaki, Sota; Ota, Hiromi; Takaishi, Kazuto.

In: Organic Letters, Vol. 19, No. 15, 04.08.2017, p. 4070-4073.

Research output: Contribution to journalArticle

Ema, Tadashi ; Yokoyama, Maki ; Watanabe, Sagiri ; Sasaki, Sota ; Ota, Hiromi ; Takaishi, Kazuto. / Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide. In: Organic Letters. 2017 ; Vol. 19, No. 15. pp. 4070-4073.
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