Induced chirality in a metal-organic framework by postsynthetic modification for highly selective asymmetric aldol reactions

Anneleen L.W. Demuynck; Maarten Goesten; Enrique V. Ramos-Fernandez; Michiel Dusselier; Jozef Vanderleyden; Freek Kapteijn; Jorge Gascon; Bert F. Sels

doi:10.1002/cctc.201402082

Induced chirality in a metal-organic framework by postsynthetic modification for highly selective asymmetric aldol reactions

Anneleen L.W. Demuynck, Maarten Goesten, Enrique V. Ramos-Fernandez, Michiel Dusselier, Jozef Vanderleyden, Freek Kapteijn, Jorge Gascon^*, Bert F. Sels

^*Corresponding author for this work

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

23 Scopus citations

Abstract

A straightforward synthetic route to chiral metal-organic frameworks is proposed that relies on an acid-base interaction between an acid linker and a chiral primary amino acid derived diamine organocatalyst. High ee values for the aldol condensation of linear ketones and aromatic aldehydes are reported with this heterogeneous catalyst. Three consecutive catalyst reuse experiments demonstrated that the majority of the activity was preserved, as was the enantioselectivity.

Original language	English (US)
Pages (from-to)	2211-2214
Number of pages	4
Journal	ChemCatChem
Volume	6
Issue number	8
DOIs	https://doi.org/10.1002/cctc.201402082
State	Published - Aug 2014
Externally published	Yes

Keywords

aldol reaction
asymmetric catalysis
heterogeneous catalysis
metal-organic frameworks
organocatalysis

ASJC Scopus subject areas

Catalysis
Inorganic Chemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/cctc.201402082

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title = "Induced chirality in a metal-organic framework by postsynthetic modification for highly selective asymmetric aldol reactions",

abstract = "A straightforward synthetic route to chiral metal-organic frameworks is proposed that relies on an acid-base interaction between an acid linker and a chiral primary amino acid derived diamine organocatalyst. High ee values for the aldol condensation of linear ketones and aromatic aldehydes are reported with this heterogeneous catalyst. Three consecutive catalyst reuse experiments demonstrated that the majority of the activity was preserved, as was the enantioselectivity.",

keywords = "aldol reaction, asymmetric catalysis, heterogeneous catalysis, metal-organic frameworks, organocatalysis",

author = "Demuynck, {Anneleen L.W.} and Maarten Goesten and Ramos-Fernandez, {Enrique V.} and Michiel Dusselier and Jozef Vanderleyden and Freek Kapteijn and Jorge Gascon and Sels, {Bert F.}",

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doi = "10.1002/cctc.201402082",

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AU - Demuynck, Anneleen L.W.

AU - Goesten, Maarten

AU - Ramos-Fernandez, Enrique V.

AU - Dusselier, Michiel

AU - Vanderleyden, Jozef

AU - Kapteijn, Freek

AU - Gascon, Jorge

AU - Sels, Bert F.

PY - 2014/8

Y1 - 2014/8

N2 - A straightforward synthetic route to chiral metal-organic frameworks is proposed that relies on an acid-base interaction between an acid linker and a chiral primary amino acid derived diamine organocatalyst. High ee values for the aldol condensation of linear ketones and aromatic aldehydes are reported with this heterogeneous catalyst. Three consecutive catalyst reuse experiments demonstrated that the majority of the activity was preserved, as was the enantioselectivity.

AB - A straightforward synthetic route to chiral metal-organic frameworks is proposed that relies on an acid-base interaction between an acid linker and a chiral primary amino acid derived diamine organocatalyst. High ee values for the aldol condensation of linear ketones and aromatic aldehydes are reported with this heterogeneous catalyst. Three consecutive catalyst reuse experiments demonstrated that the majority of the activity was preserved, as was the enantioselectivity.

KW - aldol reaction

KW - asymmetric catalysis

KW - heterogeneous catalysis

KW - metal-organic frameworks

KW - organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=84905591936&partnerID=8YFLogxK

U2 - 10.1002/cctc.201402082

DO - 10.1002/cctc.201402082

M3 - Article

AN - SCOPUS:84905591936

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VL - 6

SP - 2211

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JO - ChemCatChem

JF - ChemCatChem

IS - 8

ER -

Induced chirality in a metal-organic framework by postsynthetic modification for highly selective asymmetric aldol reactions

Abstract

Keywords

ASJC Scopus subject areas

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