Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts

Asymmetric ring-opening reactions of meso-epoxides by aromatic amines were achieved by using some chiral metal–organic frameworks. The corresponding β-amino alcohols were obtained with good yields and enantioselectivities (up to 97% ee).

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The mechanism of an asymmetric ring-opening reaction of epoxide with amine catalyzed by a metal–organic framework: insights from combined quantum mechanics and molecular mechanics calculations

Dalton Transactions ◽

10.1039/c6dt04745a ◽

2017 ◽

Vol 46 (11) ◽

pp. 3470-3481 ◽

Cited By ~ 24

Author(s):

Kazuki Doitomi ◽

Kai Xu ◽

Hajime Hirao

Keyword(s):

Quantum Mechanics ◽

Molecular Mechanics ◽

Ring Opening ◽

Metal Organic Framework ◽

Molecular Mechanics Calculations ◽

Π Interactions ◽

Ring Opening Reaction ◽

Metal Organic ◽

Asymmetric Ring Opening ◽

Asymmetric Ring Opening Reaction

QM/MM computations suggest that the asymmetric ring-opening reaction of epoxide with amine is controlled by CH–π interactions between aniline and a naphthol moiety.

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ChemInform Abstract: A Novel Chiral Porous Metal-Organic Framework: Asymmetric Ring Opening Reaction of Epoxide with Amine in the Chiral Open Space.

ChemInform ◽

10.1002/chin.200825026 ◽

2008 ◽

Vol 39 (25) ◽

Author(s):

Koichi Tanaka ◽

Shinji Oda ◽

Motoo Shiro

Keyword(s):

Ring Opening ◽

Open Space ◽

Metal Organic Framework ◽

Porous Metal ◽

Ring Opening Reaction ◽

Metal Organic ◽

Asymmetric Ring Opening ◽

Organic Framework ◽

Asymmetric Ring Opening Reaction

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Improved catalytic performance of porous metal–organic frameworks for the ring opening of styrene oxide

CrystEngComm ◽

10.1039/c7ce00528h ◽

2017 ◽

Vol 19 (29) ◽

pp. 4219-4226 ◽

Cited By ~ 11

Author(s):

Diana Julião ◽

André D. S. Barbosa ◽

Andreia F. Peixoto ◽

Cristina Freire ◽

Baltazar de Castro ◽

...

Keyword(s):

Ring Opening ◽

Heterogeneous Catalysts ◽

Metal Organic Framework ◽

Styrene Oxide ◽

Metal Organic Frameworks ◽

Porous Metal ◽

Catalytic Performance ◽

Metal Organic ◽

Organic Framework

An emerging strategy to improve the performance of porous metal–organic framework (MOF) materials as heterogeneous catalysts is reported.

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A novel chiral porous metal–organic framework: asymmetric ring opening reaction of epoxide with amine in the chiral open space

Chemical Communications ◽

10.1039/b714083e ◽

2008 ◽

pp. 820-822 ◽

Cited By ~ 156

Author(s):

Koichi Tanaka ◽

Shinji Oda ◽

Motoo Shiro

Keyword(s):

Ring Opening ◽

Open Space ◽

Metal Organic Framework ◽

Porous Metal ◽

Ring Opening Reaction ◽

Metal Organic ◽

Asymmetric Ring Opening ◽

Organic Framework ◽

Asymmetric Ring Opening Reaction

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An Overview of Metal-organic Frameworks-based Acid/Base Catalysts for Biofuel Synthesis

Current Organic Chemistry ◽

10.2174/1385272824999200726230556 ◽

2020 ◽

Vol 24 (16) ◽

pp. 1876-1891

Author(s):

Qiuyun Zhang ◽

Yutao Zhang ◽

Jingsong Cheng ◽

Hu Li ◽

Peihua Ma

Keyword(s):

Alternative Fuels ◽

Heterogeneous Catalysts ◽

Supported Catalysts ◽

Metal Organic Framework ◽

Metal Organic Frameworks ◽

Flexible Structures ◽

Biodiesel Production ◽

Biodiesel Synthesis ◽

Metal Organic ◽

Organic Framework

Biofuel synthesis is of great significance for producing alternative fuels. Among the developed catalytic materials, the metal-organic framework-based hybrids used as acidic, basic, or supported catalysts play major roles in the biodiesel production. This paper presents a timely and comprehensive review of recent developments on the design and preparation of metal-organic frameworks-based catalysts used for biodiesel synthesis from various oil feedstocks, including MILs-based catalysts, ZIFs-based catalysts, UiO-based catalysts, Cu-BTC-based catalysts, and MOFs-derived porous catalysts. Due to their unique and flexible structures, excellent thermal and hydrothermal stability, and tunable host-guest interactions, as compared with other heterogeneous catalysts, metal-organic framework-based catalysts have good opportunities for application in the production of biodiesel at industrial scale.

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