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

22 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

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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