Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide

Chihiro Maeda; Mayato Mitsuzane; Tadashi Ema

doi:10.1021/acs.orglett.9b00447

Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide

Chihiro Maeda, Mayato Mitsuzane, Tadashi Ema

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO ₂ . Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.

Original language	English
Pages (from-to)	1853-1856
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.9b00447
Publication status	Published - Mar 15 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b00447

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title = "Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide",

abstract = " Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO 2 . Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides. ",

author = "Chihiro Maeda and Mayato Mitsuzane and Tadashi Ema",

note = "Funding Information: This work was supported by JSPS KAKENHI (Grant No. JP16H01030) in Precisely Designed Catalysts with Customized Scaffolding and The Foundation for The Promotion of Ion Engineering. We thank Prof. H. Yorimitsu (Kyoto University) for mass measurements. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b00447",

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AU - Maeda, Chihiro

AU - Mitsuzane, Mayato

AU - Ema, Tadashi

N1 - Funding Information: This work was supported by JSPS KAKENHI (Grant No. JP16H01030) in Precisely Designed Catalysts with Customized Scaffolding and The Foundation for The Promotion of Ion Engineering. We thank Prof. H. Yorimitsu (Kyoto University) for mass measurements. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/3/15

Y1 - 2019/3/15

N2 - Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO 2 . Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.

AB - Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO 2 . Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.

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Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide

Abstract

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