Hemisquaramide Tweezers as Organocatalysts: Synthesis of Cyclic Carbonates from Epoxides and CO 2

Kazuto Takaishi, Takafumi Okuyama, Shota Kadosaki, Masanobu Uchiyama, Tadashi Ema

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Hemisquaramide tweezers, a new family of H-bond donor organocatalysts, are reported. The catalysts could be synthesized within two steps. Among them, H 8 -binaphthyl-linked hemisquaramide 7 markedly accelerated the synthesis of cyclic carbonates from epoxides and CO 2 . The reactions proceeded well under mild and solvent-free conditions. Kinetic resolution was also achieved at -20 °C (s = 3.0). The adjustable bite angle and orientation of the two NH groups of the catalysts are important for the high activity.

Original languageEnglish
Pages (from-to)1397-1401
Number of pages5
JournalOrganic Letters
Volume21
Issue number5
DOIs
Publication statusPublished - Mar 1 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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