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

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

doi:10.1021/acs.orglett.9b00117

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 journal › Article › peer-review

53 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 language	English
Pages (from-to)	1397-1401
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.9b00117
Publication status	Published - Mar 1 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Hemisquaramide Tweezers as Organocatalysts: Synthesis of Cyclic Carbonates from Epoxides and CO 2",

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. ",

author = "Kazuto Takaishi and Takafumi Okuyama and Shota Kadosaki and Masanobu Uchiyama and Tadashi Ema",

note = "Funding Information: This work was partly supported by JSPS KAKENHI Grant No. JP16H01030 in Precisely Designed Catalysts with Customized Scaffolding. Allotment of computational resources from HOKUSAI GreatWave (RIKEN) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b00117",

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AU - Takaishi, Kazuto

AU - Okuyama, Takafumi

AU - Kadosaki, Shota

AU - Uchiyama, Masanobu

AU - Ema, Tadashi

N1 - Funding Information: This work was partly supported by JSPS KAKENHI Grant No. JP16H01030 in Precisely Designed Catalysts with Customized Scaffolding. Allotment of computational resources from HOKUSAI GreatWave (RIKEN) is gratefully acknowledged. Publisher Copyright: © 2019 American Chemical Society.

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N2 - 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.

AB - 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.

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

Abstract

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