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

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

doi:10.1021/acs.orglett.7b01838

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 journal › Article › peer-review

42 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 language	English
Pages (from-to)	4070-4073
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.7b01838
Publication status	Published - Aug 4 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

author = "Tadashi Ema and Maki Yokoyama and Sagiri Watanabe and Sota Sasaki and Hiromi Ota and Kazuto Takaishi",

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T1 - Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide

AU - Ema, Tadashi

AU - Yokoyama, Maki

AU - Watanabe, Sagiri

AU - Sasaki, Sota

AU - Ota, Hiromi

AU - Takaishi, Kazuto

PY - 2017/8/4

Y1 - 2017/8/4

N2 - 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.

AB - 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.

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

Abstract

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