Induced Chirality in a Metal-Organic Framework by Postsynthetic Modification for Highly Selective Asymmetric Aldol Reactions

• Published in: ChemCatChem Vol. 6; no. 8; pp. 2211 - 2214
• Main Authors: Demuynck, Anneleen L. W., Goesten, Maarten G., Ramos-Fernandez, Enrique V., Dusselier, Michiel, Vanderleyden, Jozef, Kapteijn, Freek, Gascon, Jorge, Sels, Bert F.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-08-2014; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: aldol reaction; asymmetric catalysis; heterogeneous catalysis; metal-organic frameworks; organocatalysis
• ISSN: 1867-3880; 1867-3899
• DOI: 10.1002/cctc.201402082

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.
Organocatalysis with MOFs: A practical synthesis 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.